3-biphenyl-substituted-3-substituted-4-ketolactam and ketolactone and their utilization as pesticide

ABSTRACT

The present invention relates to novel 3-biphenyl-substituted, 3-substituted 4-keto-lactams and -lactones of the formula (I) 
     
       
         
         
             
             
         
       
         
         
           
             in which A, B, Q, G, W, X, Y and Z are as defined in the disclosure,
 
to processes for their preparation, and to their use as pesticides and/or microbicides and/or herbicides.

This application is a division of U.S. application Ser. No. 10/496,734,filed Oct. 12, 2004, now U.S. Pat. No. 7,307,044 which was filed under35 U.S.C. 371 as a national stage application of PCT/EP02/12881, filedNov. 18, 2002, which was published in German as International PatentPublication WO 03/045957 on Jun. 5, 2003, which is entitled to the rightof priority of German Patent Application 101 58 560.8, filed Nov. 29,2001.

The invention relates to novel 3-biphenyl-substituted, 3-substituted4-ketolactams and -lactones, to processes and intermediates for theirpreparation and to their use as pesticides, microbicides and/orherbicides.

It is already known that certain phenyl-substituted 3-halo-4-ketolactams(JP-A-10-258 555) and phenyl-substituted 3-halo-4-ketolactones(JP-A-10-258 555) act as acaricides, insecticides and/or herbicides.

However, in particular at low application rates and concentrations, theactivity and activity spectrum of these compounds is not always entirelysatisfactory. Furthermore, the compatibility of these compounds with thecrop plants is not always sufficient.

This invention now provides novel compounds of the formula (I)

in which

-   -   Q represents oxygen, sulphur or the group N-D,    -   X represents halogen, alkyl, alkoxy, alkenyloxy, alkylthio,        alkylsulphinyl, alkylsulphonyl, haloalkyl, haloalkoxy,        haloalkenyloxy, nitro, cyano or optionally substituted phenyl,    -   Y represents in each case optionally substituted aryl or        hetaryl,    -   W and Z independently of one another represent hydrogen,        halogen, alkyl, alkoxy, haloalkyl, haloalkoxy, nitro or cyano,    -   A represents hydrogen, in each case optionally substituted        alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl, alkylthioalkyl,        saturated or unsaturated, optionally substituted cycloalkyl, in        which optionally at least one ring atom is replaced by a        heteroatom, or represents in each case optionally halogen-,        alkyl-, haloalkyl-, alkoxy-, haloalkoxy-, cyano- or        nitro-substituted aryl, arylalkyl or hetaryl,    -   B represents hydrogen, alkyl or alkoxyalkyl, or    -   A and B together with the carbon atom to which they are attached        represent a saturated or unsaturated, unsubstituted or        substituted cycle which optionally contains at least one        heteroatom,    -   D represents hydrogen or an optionally substituted radical from        the group consisting of alkyl, alkenyl, alkynyl, alkoxyalkyl,        polyalkoxyalkyl, alkylthioalkyl, saturated or unsaturated        cycloalkyl, in which optionally one or more ring members are        replaced by heteroatoms, arylalkyl, aryl, hetarylalkyl or        hetaryl or    -   A and D together with the atoms to which they are attached        represent a saturated or unsaturated ring which optionally        contains at least one heteroatom and is unsubstituted or        substituted in the A, D moiety,    -   G represents halogen or nitro.

Depending inter alia on the nature of the substituents, the compounds ofthe formula (I) can be present as geometrical and/or optical isomers orisomer mixtures of varying composition which, if appropriate, can beseparated in a customary manner. The present invention provides both thepure isomers and the isomer mixtures, their preparation and use andcompositions comprising them. However, hereinbelow, for the sake ofsimplicity, compounds of the formula (I) are always referred to,although this is meant to include both the pure compounds and, ifappropriate, mixtures having varying proportions of isomeric compounds.

Including the meanings of Q, the following principal structures (I-1) to(I-3):

result, in which

-   -   A, B, D, G, W, X, Y and Z are as defined above.    -   A) Furthermore, it has been found that compounds of the formulae        (I-1) to (I-3)

-   -   -   in which A, B, Q, W, X, Y and Z, are as defined above        -   and        -   G represents halogen, preferably chlorine and bromine,        -   are obtained when compounds of the formulae (II-1) to (II-3)

-   -   -   in which A, B, Q, W, X, Y and Z are as defined above        -   are reacted with halogenating agents in the presence of a            solvent and, if appropriate, in the presence of a            free-radical initiator.

    -   B) Furthermore, compounds of the formulae (I-1) to (I-3)

-   -   -   in which A, B, Q, W, X, Y and Z are as defined above        -   and        -   G represents nitro,        -   are obtained when compounds of the formulae (II-1) to (II-3)

-   -   -   in which        -   A, B, Q, W, X, Y and Z are as defined above        -   are reacted with nitrating agents, such as, for example,            fuming nitric acid, in the presence of a solvent.

The compounds of the formulae (II-1) to (II-3)

in which

-   -   A, B, Q, W, X, Y and Z are as defined above,    -   which compounds are required for processes A and B, are known        compounds (WO 99/43649, WO 99/48869, WO 99/55673), or they can        be synthesized by the processes described therein.

Suitable halogenating agents for process A are, for example, sulphurylchloride, sulphuryl bromide, thionyl chloride, thionyl bromide, imides,such as, for example, N-bromosuccinimide or N-chlorosuccinimide,chlorosulphonic acid, and also hypochlorites, such as, for example,tert-butyl hypochlorite.

Suitable nitrating agents for process B are fuming nitric acid, and also“nitrating acid mixtures”.

Furthermore, it has been found that the novel compounds of the formula(I) have very good activity as pesticides, preferably as insecticides,acaricides and/or fungicides, and/or as herbicides.

The formula (I) provides a general definition of the compounds accordingto the invention. Preferred substituents or ranges of the radicalslisted in the formulae mentioned above and below are illustrated below:

-   -   Q preferably represents oxygen, sulphur or the group N-D,    -   W preferably represents hydrogen, halogen, C₁-C₆-alkyl or        C₁-C₆-alkoxy,    -   X preferably represents halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,        C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, cyano or optionally halogen-,        C₁-C₆-alkyl-, C₁-C₆-alkoxy-, C₁-C₄-haloalkyl-,        C₁-C₄-haloalkoxy-, nitro- or cyano-substituted phenyl,    -   Y preferably represents one of the radicals

-   -   V¹ preferably represents hydrogen, halogen, C₁-C₁₂-alkyl,        C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylsulphinyl,        C₁-C₆-alkylsulphonyl, C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy, nitro,        cyano or phenyl which is optionally mono- or disubstituted by        halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₄-haloalkyl,        C₁-C₄-haloalkoxy, nitro or cyano,    -   V² and V³ independently of one another preferably represent        hydrogen, halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₄-haloalkyl or        C₁-C₄-haloalkoxy,    -   Z preferably represents hydrogen, halogen, C₁-C₆-alkyl,        C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, nitro or cyano,    -   A preferably represents in each case optionally        halogen-substituted C₁-C₁₂-alkyl, C₃-C₈-alkenyl,        C₁-C₁₀-alkoxy-C₁-C₈-alkyl, poly-C₁-C₈-alkoxy-C₁-C₈-alkyl,        C₁-C₁₀-alkylthio-C₁-C₆-alkyl, optionally halogen-, C₁-C₆-alkyl-        or C₁-C₆-alkoxy-substituted C₃-C₈-cycloalkyl in which optionally        one or two not directly adjacent ring members are replaced by        oxygen and/or sulphur or represents in each case optionally        halogen-, C₁-C₆-alkyl-, C₁-C₆-haloalkyl-, C₁-C₆-alkoxy-,        C₁-C₆-haloalkoxy-, cyano- or nitro-substituted phenyl,        phenyl-C₁-C₆-alkyl, or represents hydrogen if in the case of        group (I-1) D is not hydrogen,    -   B preferably represents hydrogen, C₁-C₁₂-alkyl or        C₁-C₈-alkoxy-C₁-C₆-alkyl, or    -   A, B and the carbon atom to which they are attached preferably        represent saturated C₃-C₁₀-cycloalkyl or unsaturated        C₅-C₁₀-cycloalkyl in which optionally one ring member is        replaced by oxygen or sulphur and which is optionally mono- or        disubstituted by C₁-C₈-alkyl, C₃-C₁₀-cycloalkyl,        C₁-C₆-haloalkyl, C₁-C₈-alkoxy, C₁-C₈-alkylthio, halogen or        phenyl, or    -   A, B and the carbon atom to which they are attached preferably        represent C₃-C₆-cycloalkyl which is substituted by an        alkylenediyl group which optionally contains one or two not        directly adjacent oxygen and/or sulphur atoms, or by an        alkylenedioxyl or by an alkylenedithioyl group which, together        with the carbon atom to which it is attached, forms a further        five- to eight-membered ring, or    -   A, B and the carbon atom to which they are attached preferably        represent C₃-C₈-cycloalkyl or C₅-C₈-cycloalkenyl in which two        substituents together with the carbon atoms to which they are        attached represent in each case optionally C₁-C₆-alkyl-,        C₁-C₆-alkoxy- or halogen-substituted C₂-C₆-alkanediyl,        C₂-C₆-alkenediyl or C₄-C₆-alkanediendiyl in which optionally one        methylene group is replaced by oxygen or sulphur,    -   D preferably represents hydrogen, in each case optionally        halogen-substituted C₁-C₁₂-alkyl, C₃-C₈-alkenyl, C₃-C₈-alkynyl,        C₁-C₁₀-alkoxy-C₂-C₈-alkyl, poly-C₁-C₈-alkoxy-C₂-C₈-alkyl,        C₁-C₁₀-alkylthio-C₂-C₈-alkyl, optionally halogen-, C₁-C₄-alkyl-,        C₁-C₄-alkoxy- or C₁-C₄-haloalkyl-substituted C₃-C₈-cycloalkyl in        which optionally one ring member is replaced by oxygen or        sulphur or represents optionally halogen-, C₁-C₆-alkyl-,        C₁-C₆-haloalkyl-, C₁-C₆-alkoxy-, C₁-C₆-haloalkoxy-, cyano- or        nitro-substituted phenyl,    -   A and D together preferably represent in each case optionally        substituted C₃-C₆-alkanediyl or C₃-C₆-alkenediyl in which        optionally one methylene group is replaced by oxygen or sulphur,        -   possible substituents being in each case:        -   C₁-C₆-alkyl, C₁-C₆-alkoxy or a further C₃-C₆-alkanediyl            grouping,    -   G preferably represents chlorine, bromine or nitro.

In the radical definitions mentioned as being preferred, halogenrepresents fluorine, chlorine, bromine and iodine, in particularfluorine, chlorine and bromine.

-   -   Q particularly preferably represents oxygen, sulphur or the        group N-D,    -   W particularly preferably represents hydrogen, chlorine, bromine        or C₁-C₄-alkyl,    -   X particularly preferably represents fluorine, chlorine,        bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkyl,        C₁-C₄-haloalkoxy or cyano,    -   Y particularly preferably represents the radical

-   -   V¹ particularly preferably represents hydrogen, fluorine,        chlorine, bromine, C₁-C₆-alkyl, C₁-C₄-alkoxy, C₁-C₂-haloalkyl,        C₁-C₂-haloalkoxy, nitro or cyano, or represents phenyl which is        optionally mono- or disubstituted by fluorine, chlorine,        bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₂-haloalkyl,        C₁-C₂-haloalkoxy, nitro or cyano,    -   V² particularly preferably represents hydrogen, fluorine,        chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₂-haloalkyl or        C₁-C₂-haloalkoxy,    -   Z particularly preferably represents hydrogen, fluorine,        chlorine, bromine, C₁-C₄-alkyl, C₁-C₂-haloalkyl, C₁-C₄-alkoxy or        C₁-C₂-haloalkoxy,    -   A particularly preferably represents C₁-C₁₀-alkyl,        C₁-C₈-alkoxy-C₁-C₆-alkyl, each of which is optionally mono- to        pentasubstituted by fluorine or chlorine, represents        C₃-C₇-cycloalkyl which is optionally mono- or disubstituted by        fluorine, chlorine, C₁-C₄-alkyl or C₁-C₄-alkoxy and in which        optionally one ring member is replaced by oxygen or sulphur, or        represents phenyl or phenyl-C₁-C₄-alkyl, each of which is        optionally mono- or disubstituted by fluorine, chlorine,        bromine, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or        C₁-C₄-haloalkoxy, or represents hydrogen if in the case of the        group (I-1) D is not hydrogen,    -   B particularly preferably represents hydrogen or C₁-C₆-alkyl, or    -   A, B and the carbon atom to which they are attached particularly        preferably represent saturated C₃-C₈-cycloalkyl in which        optionally one ring member is replaced by oxygen or sulphur and        which is optionally mono- or disubstituted by C₁-C₆-alkyl,        C₅-C₆-cycloalkyl, C₁-C₃-haloalkyl, C₁-C₆-alkoxy, fluorine,        chlorine or phenyl, with the proviso that D in group (I-1)        represents hydrogen or C₁-C₄-alkyl,    -   D particularly preferably represents hydrogen, represents        C₁-C₁₀-alkyl, C₃-C₆-alkenyl, C₁-C₄-alkoxy-C₂-C₄-alkyl or        C₁-C₄-alkylthio-C₂-C₄-alkyl, each of which is optionally mono-        to pentasubstituted by fluorine or chlorine, represents        C₃-C₇-cycloalkyl which is optionally mono- or disubstituted by        fluorine, chlorine, C₁-C₄-alkyl, C₁-C₄-alkoxy or C₁-C₂-haloalkyl        and in which optionally one methylene group is replaced by        oxygen or sulphur, or represents phenyl which is optionally        mono- or disubstituted by fluorine, chlorine, bromine,        C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy,        or    -   A and D together particularly preferably represent optionally        substituted C₃-C₅-alkanediyl in which one methylene group may be        replaced by oxygen or sulphur, possible substituents being        C₁-C₄-alkyl,    -   G particularly preferably represents chlorine, bromine or nitro.

In the radical definitions mentioned as being particularly preferred,halogen represents fluorine, chlorine, bromine and iodine, in particularfluorine, chlorine and bromine.

-   -   Q very particularly preferably represents oxygen, sulphur or the        group N-D,    -   W very particularly preferably represents hydrogen, chlorine,        methyl or ethyl,    -   X very particularly preferably represents chlorine, methyl,        ethyl, n-propyl, isopropyl, methoxy, ethoxy, n-propoxy,        isopropoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy        or cyano,    -   Y very particularly preferably represents the radical

-   -   V¹ very particularly preferably represents hydrogen, fluorine,        chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, n-butyl,        isobutyl, tert-butyl, methoxy, ethoxy, n-propoxy, isopropoxy,        trifluoromethyl, trifluoromethoxy, nitro or cyano,    -   V² very particularly preferably represents hydrogen, fluorine,        chlorine, methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy,        trifluoromethyl or trifluoromethoxy,    -   Z very particularly preferably represents hydrogen, fluorine,        chlorine, methyl, ethyl, n-propyl or methoxy,    -   A very particularly preferably represents C₁-C₆-alkyl or        C₁-C₂-alkoxy-C₁-C₂-alkyl, C₃-C₆-cycloalkyl in which optionally        one ring member is replaced by oxygen or sulphur or represents        hydrogen if in the case of the group (I-1) D is not hydrogen,    -   B very particularly preferably represents hydrogen, methyl,        ethyl, or    -   A, B and the carbon atom to which they are attached very        particularly preferably represent saturated C₃-C₈-cycloalkyl in        which optionally one ring member is replaced by oxygen or        sulphur and which is optionally monosubstituted by methyl,        ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl,        trifluoromethyl, methoxy, ethoxy, n-propoxy, isopropoxy,        n-butoxy or isobutoxy, with the proviso that D in group (I-1)        represents hydrogen or C₁-C₃-alkyl,    -   D very particularly preferably represents hydrogen, methyl,        ethyl, n-propyl, isopropyl, cyclopropyl, cyclopentyl or        cyclohexyl, especially preferably hydrogen,    -   A, D together very particularly preferably represent optionally        substituted C₃-C₄-alkanediyl in which optionally one carbon atom        is replaced by oxygen or sulphur,    -   G very particularly preferably represents chlorine or nitro,        especially preferably chlorine.

Especially preferred are compounds of the formula (I-1) in which

-   -   W especially preferably represents hydrogen, chlorine or methyl,    -   X especially preferably represents chlorine, methyl or ethyl,    -   Y especially preferably represents the radical

-   -   V¹ especially preferably represents chlorine or methyl,    -   V² especially preferably represents hydrogen or chlorine,    -   Z especially preferably represents hydrogen or methyl,    -   A especially preferably represents methyl, ethyl, propyl,        isopropyl, n-butyl, isobutyl, s-butyl, tert-butyl, cyclopropyl,        cyclopentyl or cyclohexyl (in particular methyl or isopropyl),    -   B especially preferably represents methyl,    -   A, B and the carbon atom to which they are attached especially        preferably represent saturated C₃-C₈-cycloalkyl in which        optionally one ring member is replaced by oxygen or sulphur and        which is optionally monosubstituted by methyl or, in the case of        C₆-cycloalkyl, also by ethyl, n-propyl, isopropyl, n-butyl,        isobutyl, tert-butyl, trifluoromethyl, methoxy, ethoxy,        n-propoxy, isopropoxy, n-butoxy or isobutoxy (in particular C₃-,        C₅- or C₆-cycloalkyl where, in the case of C₆-cycloalkyl,        optionally one ring atom is replaced by oxygen and which are        optionally monosubstituted by methyl, ethyl, n-propyl,        isopropyl, methoxy or ethoxy),    -   D especially preferably represents hydrogen,    -   G especially preferably represents chlorine or nitro (in        particular chlorine).

Especially preferred are compounds of the formula (I-2) in which

-   -   W especially preferably represents hydrogen, chlorine or methyl        (in particular hydrogen or methyl),    -   X especially preferably represents chlorine, methyl or ethyl (in        particular methyl or ethyl),    -   Y especially preferably represents the radical

-   -   V¹ especially preferably represents chlorine, fluorine, cyano or        methyl,    -   V² especially preferably represents hydrogen or chlorine,    -   Z especially preferably represents hydrogen or methyl,    -   A especially preferably represents methyl, ethyl, propyl,        isopropyl, n-butyl, isobutyl, s-butyl, tert-butyl, cyclopropyl,        cyclopentyl or cyclohexyl (in particular methyl or isopropyl),    -   B especially preferably represents methyl, or    -   A, B and the carbon atom to which they are attached especially        preferably represent saturated C₃-C₈-cycloalkyl in which        optionally one ring member is replaced by oxygen or sulphur and        which is optionally monosubstituted by methyl or, in the case of        C₆-cycloalkyl, also by ethyl, n-propyl, isopropyl, n-butyl,        isobutyl, tert-butyl, trifluoromethyl, methoxy, ethoxy,        n-propoxy, isopropoxy, n-butoxy or isobutoxy (in particular C₅-        or C₆-cycloalkyl where, in the case of C₆-cycloalkyl, optionally        one ring atom is replaced by oxygen and which is optionally        monosubstituted by methyl, trifluoromethyl, methoxy or ethoxy),    -   G especially preferably represents chlorine.

Especially preferred are compounds of the formula (I-3) in which

-   -   W especially preferably represents hydrogen,    -   X especially preferably represents chlorine or methyl, (in        particular methyl),    -   Y especially preferably represents the radical

-   -   Z especially preferably represents hydrogen or methyl,    -   A, B and the carbon atom to which they are attached especially        preferably represent saturated C₅-C₆-cycloalkyl in which        optionally one ring member is replaced by oxygen and which is        optionally substituted by methyl or methoxy (in particular        C₆-cycloalkyl)    -   G especially preferably represents chlorine.

The general or preferred radical definitions or illustrations listedabove can be combined with one another as desired, i.e. includingcombinations between the respective ranges and preferred ranges. Thedefinitions apply both to the end products and, correspondingly, toprecursors and intermediates.

Preference according to the invention is given to the compounds of theformula (I) which contain a combination of the meanings listed above asbeing preferred (preferable).

Particular preference according to the invention is given to thecompounds of the formula (I) which contain a combination of the meaningslisted above as being particularly preferred.

Very particular preference according to the invention is given to thecompounds of the formula (I) which contain a combination of the meaningslisted above as being very particularly preferred.

Saturated or unsaturated hydrocarbon radicals, such as alkyl or alkenyl,can in each case be straight-chain or branched as far as this ispossible, including in combination with heteroatoms, such as, forexample, an alkoxy.

Unless indicated otherwise, optionally substituted radicals can be mono-or polysubstituted where, in the case of polysubstitution, thesubstituents can be identical or different.

In addition to the compounds mentioned in the Preparation Examples, thefollowing compounds of the formula (I-1) may be specifically mentioned:

TABLE 1 A B D CH₃ H H C₂H₅ H H C₃H₇ H H i-C₃H₇ H H C₄H₉ H H i-C₄H₉ H Hs-C₄H₉ H H t-C₄H₉ H H CH₃ CH₃ H C₂H₅ CH₃ H C₃H₇ CH₃ H i-C₃H₇ CH₃ H C₄H₉CH₃ H i-C₄H₉ CH₃ H s-C₄H₉ CH₃ H t-C₄H₉ CH₃ H C₂H₅ C₂H₅ H

CH₃ H

CH₃ H

CH₃ H —(CH₂)₂— H —(CH₂)₄— H —(CH₂)₅— H —(CH₂)₆— H —(CH₂)₇— H—(CH₂)₂—O—(CH₂)₂— H —CH₂—O—(CH₂)₃— H —(CH₂)₂—S—(CH₂)₂— H—CH₂—CHCH₃—(CH₂)₃— H —(CH₂)₂—CHCH₃—(CH₂)₂— H —(CH₂)₂—CHC₂H₅—(CH₂)₂— H—(CH₂)₂—CHC₃H₇—(CH₂)₂— H —(CH₂)₂—CHi-C₃H₇—(CH₂)₂— H—(CH₂)₂—CHOCH₃—(CH₂)₂— H —(CH₂)₂—CHOC₂H₅—(CH₂)₂— H—(CH₂)₂—CHOC₃H₇—(CH₂)₂— H —(CH₂)₂—CHOi-C₃H₇—(CH₂)₂— H—(CH₂)₂—C(CH₃)₂—(CH₂)₂— H —CH₂—(CHCH₃)₂—(CH₂)₂— H A D B —(CH₂)₃— H—(CH₂)₄— H —CH₂—CHCH₃—CH₂— H —CH₂—CH₂—CHCH₃— H —CH₂—CHCH₃—CHCH₃— H—CH₂—S—CH₂— H —CH₂—S—(CH₂)₂— H —(CH₂)₂—S—CH₂— H

H H CH₃ H H C₂H₅ H H C₃H₇ H H i-C₃H₇ H H

H H

H H

H H CH₃ CH₃ H C₂H₅ CH₃ H C₃H₇ CH₃ H i-C₃H₇ CH₃ H

CH₃ H

CH₃ H

CH₃ H CH₃ C₂H₅ H C₂H₅ C₂H₅ W = H; X = CH₃, V¹ = H, V² = H, Z = H

Table 2: A, B and D are as stated in Table 1

-   -   W═H; X═CH₃; Z=4-CH₃; V¹═H; V²═H.

Table 3: A, B and D are as stated in Table 1

-   -   W═CH₃; X═CH₃; Z=4-CH₃; V¹═H; V²═H.

Table 4: A, B and D are as stated in Table 1

-   -   W═H; X═CH₃; Z═H; V¹=4-Cl; V²═H.

Table 5: A, B and D are as stated in Table 1

-   -   W═H; X═CH₃; Z=4-CH₃; V¹=4-Cl; V²═H.

Table 6: A, B and D are as stated in Table 1

-   -   W═CH₃; X═CH₃; Z=4-CH₃; V¹=4-Cl; V²═H.

Table 7: A, B and D are as stated in Table 1

-   -   W═H; X═CH₃; Z═H; V¹=3-Cl; V²═H.

Table 8: A, B and D are as stated in Table 1

-   -   W═H; X═CH₃; Z=4-CH₃; V¹=3-Cl; V²═H.

Table 9: A, B and D are as stated in Table 1

-   -   W═CH₃; X═CH₃; Z=4-CH₃; V¹=3-Cl; V²═H.

Table 10: A, B and D are as stated in Table 1

-   -   W═H; X═CH₃; Z═H; V¹=3-Cl; V²=4-Cl.

Table 11: A, B and D are as stated in Table 1

-   -   W═H; X═CH₃; Z=4-CH₃; V¹=3-Cl; V²=4-Cl.

Table 12: A, B and D are as stated in Table 1

-   -   W═CH₃; X═CH₃; Z=4-CH₃; V¹=3-Cl; V²=4-Cl.

Table 13: A, B and D are as stated in Table 1

-   -   W═H; X═CH₃; Z═H; V¹=4-CF₃; V²═H.

Table 14: A, B and D are as stated in Table 1

-   -   W═H; X═CH₃; Z=4-CH₃; V¹=4-CF₃; V²═H.

Table 15: A, B and D are as stated in Table 1

-   -   W═CH₃; X═CH₃; Z=4-CH₃; V¹=4-CF₃; V²H.

Table 16: A, B and D are as stated in Table 1

-   -   W═H; X═CH₃; Z═H; V¹=4-CH₃; V²═H.

Table 17: A, B and D are as stated in Table 1

-   -   W═H; X═CH₃; Z=4-CH₃; V¹=4-CH₃; V²═H.

Table 18: A, B and D are as stated in Table 1

-   -   W═CH₃; X═CH₃; Z=4-CH₃; V¹=4-CH₃; V²═H.

Table 19: A, B and D are as stated in Table 1

-   -   W═H; X═CH₃; Z═H; V¹=4-OCH₃; V²═H.

Table 20: A, B and D are as stated in Table 1

-   -   W═H; X═CH₃; Z=4-CH₃; V¹=4-OCH₃; V²═H.

Table 21: A, B and D are as stated in Table 1

-   -   W═CH₃; X═CH₃; Z=4-CH₃; V¹=4-OCH₃; V²═H.

In addition to the compounds mentioned in the Preparation Examples, thefollowing compounds of the formula (I-2) may be specifically mentioned:

TABLE 22 A B CH₃ H C₂H₅ H C₃H₇ H i-C₃H₇ H C₄H₉ H i-C₄H₉ H s-C₄H₉ Ht-C₄H₉ H CH₃ CH₃ C₂H₅ CH₃ C₃H₈ CH₃ i-C₃H₇ CH₃ C₄H₉ CH₃ i-C₄H₉ CH₃ s-C₄H₉CH₃ t-C₄H₉ CH₃ C₂H₅ C₂H₅

CH₃

CH₃

CH₃ —(CH₂)₂— —(CH₂)₄— —(CH₂)₅— —(CH₂)₆— —(CH₂)₇— —(CH₂)₂—O—(CH₂)₂——CH₂—O—(CH₂)₃— —(CH₂)₂—S—(CH₂)₂— —CH₂—CHCH₃—(CH₂)₃——(CH₂)₂—CHCH₃—(CH₂)₂— (CH₂)₂—CHC₂H₅—(CH₂)₂— —(CH₂)₂—CHC₃H₇—(CH₂)₂——(CH₂)₂—CHi-C₃H₇—(CH₂)₂— —(CH₂)₂—CHOCH₃—(CH₂)₂— —(CH₂)₂—CHOC₂H₅—(CH₂)₂——(CH₂)₂—CHOC₃H₇—(CH₂)₂— —(CH₂)₂—CHOi-C₃H₇—(CH₂)₂——(CH₂)₂—C(CH₃)₂—(CH₂)₂— —CH₂—(CHCH₃)₂—(CH₂)₂—

W = H; X = CH₃; Z = H, V¹ = H, V² = H.

Table 23: A and B are as stated in Table 22

-   -   W═H; X═CH₃; Z=4-CH₃; V¹═H; V²═H.

Table 24: A and B are as stated in Table 22

-   -   W═CH₃; X═CH₃; Z=4-CH₃; V¹═H; V²═H.

Table 25: A and B are as stated in Table 22

-   -   W═H; X═CH₃; Z═H; V¹=4-Cl; V²═H.

Table 26: A and B are as stated in Table 22

-   -   W═H; X═CH₃; Z=4-CH₃; V¹=4-Cl; V²═H.

Table 27: A and B are as stated in Table 22

-   -   W═CH₃; X═CH₃; Z=4-CH₃; V¹=4-Cl; V²═H.

Table 28: A and B are as stated in Table 22

-   -   W═H; X═CH₃; Z═H; V¹=3-Cl; V²═H.

Table 29: A and B are as stated in Table 22

-   -   W═H; X═CH₃; Z=4-CH₃; V¹=3-Cl; V²═H.

Table 30: A and B are as stated in Table 22

-   -   W═CH₃; X═CH₃; Z=4-CH₃; V¹=3-Cl; V²═H.

Table 31: A and B are as stated in Table 22

-   -   W═H, X═CH₃; Z═H; V¹=4-CF₃; V²═H.

Table 32: A and B are as stated in Table 22

-   -   W═H; X═CH₃; Z=4-CH₃; V¹=4-CF₃; V²═H.

Table 33: A and B are as stated in Table 22

-   -   W═CH₃; X═CH₃; Z=4-CH₃; V¹=4-CF₃; V²═H.

Table 34: A and B are as stated in Table 22

-   -   W═H; X═CH₃; Z═H; V¹=3-Cl; V²=4-Cl.

Table 35: A and B are as stated in Table 22

-   -   W═H; X═CH₃; Z=4-CH₃; V¹=3-Cl; V²=4-Cl.

Table 36: A and B are as stated in Table 22

-   -   W═CH₃; X═CH₃; Z=4-CH₃; V¹=3-Cl; V¹=4-Cl.

Table 37: A and B are as stated in Table 22

-   -   W═H; X═CH₃; Z═H; V¹=4-CH₃; V²═H.

Table 38: A and B are as stated in Table 22

-   -   W═H; X═CH₃; Z=4-CH₃; V¹=4-CH₃; V²═H.

Table 39: A and B are as stated in Table 22

-   -   W═CH₃; X═CH₃; Z=4-CH₃; V¹=4-CH₃; V²═H.

Table 40: A and B are as stated in Table 22

-   -   W═H; X═CH₃; Z═H; V¹=4-OCH₃; V²═H.

Table 41: A and B are as stated in Table 22

-   -   W═H; X═CH₃; Z=4-CH₃; V¹=4-OCH₃; V²═H.

Table 42: A and B are as stated in Table 22

-   -   W═CH₃; X═CH₃; Z=4-CH₃; V¹=4-OCH₃; V²═H.

Using, according to process (A),3-[(2-methyl-5-phenyl)phenyl]-5,5-pentamethylene-4-hydroxy-Δ³-pyrrolidin-2-oneas starting material, the course of the process according to theinvention can be represented by the following reaction scheme:

Using, according to process (B),3-[(2-methyl-5-(4-chloro)phenyl)phenyl]-4-hydroxy-5,5-dimethyl-Δ³-furan-2-one,the course of the process according to the invention can be representedby the following reaction scheme:

The process (A) is characterized in that compounds of the formula (II)in which A, B, Q, W, X, Y and Z are as defined above are reacted in thepresence of a diluent and a halogenating agent and, if appropriate, afree-radical initiator. Suitable free-radical initiators are, forexample, benzoyl peroxide or azobisisobutyronitrile.

Suitable diluents for use in the process (A) according to the inventionare all inert organic solvents. Preference is given to usinghydrocarbons, such as benzene, toluene and xylene, furthermore ethers,such as dibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl etherand diglycol dimethyl ether, moreover halogenated hydrocarbons, such asdichloromethane, chloroform, carbon tetrachloride, dichloroethane,chlorobenzene, dichlorobenzene, and also esters, such as ethyl acetate.

Suitable halogenating agents for process (A) are, for example, sulphurylchloride, thionyl chloride, thionyl bromide, imides, such as, forexample, N-bromosuccinimide and N-chlorosuccinmide, furthermorechlorosulphonic acid, and also hypochlorites, such as, for example,tert-butyl hypochlorite.

When carrying out the process (A) according to the invention, thereaction temperatures can be varied within a relatively wide range. Ingeneral, the process is carried out at temperatures between −40° C. and150° C., preferably between 0° C. and 100° C.

The process (A) according to the invention is generally carried outunder atmospheric pressure.

When carrying out the process (A) according to the invention, thereaction components of the formula (II) and the halogenating agents aregenerally employed in approximately equimolar amounts. However, it isalso possible to use a relatively large excess (up to 3 mol) of onecomponent or the other.

The process (B) is characterized in that compounds of the formula (II)in which A, B, Q, W, X, Y and Z are as defined above is reacted in thepresence of a diluent and in the presence of a nitrating agent.

Suitable diluents for use in the process (B) according to the inventionare all inert organic solvents. Preference is given to using halogenatedhydrocarbons, such as methylene chloride, chloroform, dichlorobenzeneand dichloroethane.

Suitable nitrating agents are “nitrating acids”, preferably fumingnitric acid.

When carrying out the process (B) according to the invention, thereaction temperatures can be varied within a relatively wide range. Ingeneral, the process is carried out at temperatures between −50° C. and150° C., preferably between 0° C. and 80° C.

The process (B) according to the invention is generally carried outunder atmospheric pressure.

When carrying out the process (B) according to the invention, thereaction components of the formula (II) and the nitrating agent aregenerally employed in approximately equimolar amounts. However, it isalso possible to use a relatively large excess (up to 5 mol) of onecomponent or the other.

The active compounds are suitable for protecting plants and plantorgans, for increasing the harvest yields, for improving the quality ofthe harvested goods and for controlling animal pests, in particularinsects, arachnids and nematodes, which are encountered in agriculture,in forests, in gardens and leisure facilities, in the protection ofstored products and of materials, and in the hygiene sector, and havegood plant tolerance, favourable toxicity to warm-blooded animals andgood environmental compatibility. They may preferably be employed ascrop protection agents. They are active against normally sensitive andresistant species and against all or some stages of development. Theabovementioned pests include:

From the order of the Isopoda, for example, Oniscus asellus,Armadillidium vulgare and Porcellio scaber.

From the order of the Diplopoda, for example, Blaniulus guttulatus.

From the order of the Chilopoda, for example, Geophilus carpophagus andScutigera spp.

From the order of the Symphyla, for example, Scutigerella immaculata.

From the order of the Thysanura, for example, Lepisma saccharina.

From the order of the Collembola, for example, Onychiurus armatus.

From the order of the Orthoptera, for example, Acheta domesticus,Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus spp. andSchistocerca gregaria.

From the order of the Blattaria, for example, Blatta orientalis,Periplaneta americana, Leucophaea maderae, Blattella germanica.

From the order of the Dermaptera, for example, Forficula auricularia.

From the order of the Isoptera, for example, Reticulitermes spp.

From the order of the Phthiraptera, for example, Pediculus humanuscorporis, Haematopinus spp., Linognathus spp., Trichodectes spp. andDamalinia spp.

From the order of the Thysanoptera, for example, Hercinothripsfemoralis, Thrips tabaci, Thrips palmi and Frankliniella accidentalis.

From the order of the Heteroptera, for example, Eurygaster spp.,Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodniusprolixus and Triatoma spp.

From the order of the Homoptera, for example, Aleurodes brassicae,Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicorynebrassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosomalanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus spp.,Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi,Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecaniumcorni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens,Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. and Psyllaspp.

From the order of the Lepidoptera, for example, Pectinophoragossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletisblancardella, Hyponomeuta padella, Plutella xylostella, Malacosomaneustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrixthurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltiaspp., Earias insulana, Heliothis spp., Mamestra brassicae, Panolisflammea, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pierisspp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleriamellonella, Tineola bisselliella, Tinea pellionella, Hofmannophilapseudospretella, Cacoecia podana, Capua reticulana, Choristoneurafumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana,Cnaphalocerus spp., Oulema oryzae.

From the order of the Coleoptera, for example, Anobium punctatum,Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus,Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedoncochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachnavarivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp.,Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus,Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogodermaspp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus,Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp.,Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha,Amphimallon solstitialis, Costelytra zealandica and Lissorhoptrusoryzophilus.

From the order of the Hymenoptera, for example, Diprion spp., Hoplocampaspp., Lasius spp., Monomorium pharaonis and Vespa spp.

From the order of the Diptera, for example, Aedes spp., Anopheles spp.,Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphoraerythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp.,Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp.,Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinellafrit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae,Tipula paludosa, Hylemyia spp. and Liriomyza spp.

From the order of the Siphonaptera, for example, Xenopsylla cheopis andCeratophyllus spp.

From the class of the Arachnida, for example, Scorpio maurus,Latrodectus mactans, Acarus siro, Argas spp., Ornithodoros spp.,Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora,Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp.,Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemusspp., Bryobia praetiosa, Panonychus spp., Tetranychus spp.,Hemitarsonemus spp., Brevipalpus spp.

The phytoparasitic nematodes include, for example, Pratylenchus spp.,Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans,Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp.,Longidorus spp., Xiphinema spp., Trichodorus spp., Bursaphelenchus spp.

If appropriate, the compounds according to the invention can, at certainconcentrations or application rates, also be used as herbicides ormicrobicides, for example as fungicides, antimycotics and bactericides.If appropriate, they can also be employed as intermediates or precursorsfor the synthesis of other active compounds.

All plants and plant parts can be treated in accordance with theinvention. Plants are to be understood as meaning in the present contextall plants and plant populations such as desired and undesired wildplants or crop plants (including naturally occurring crop plants). Cropplants can be plants which can be obtained by conventional plantbreeding and optimization methods or by biotechnological and recombinantmethods or by combinations of these methods, including the transgenicplants and inclusive of the plant cultivars protectable or notprotectable by plant breeders' rights. Plant parts are to be understoodas meaning all parts and organs of plants above and below the ground,such as shoot, leaf, flower and root, examples which may be mentionedbeing leaves, needles, stalks, stems, flowers, fruit bodies, fruits,seeds, roots, tubers and rhizomes. The plant parts also includeharvested material, and vegetative and generative propagation material,for example cuttings, tubers, rhizomes, offsets and seeds.

Treatment according to the invention of the plants and plant parts withthe active compounds is carried out directly or by allowing thecompounds to act on their surroundings, environment or storage space bythe customary treatment methods, for example by immersion, spraying,evaporation, fogging, scattering, painting on and, in the case ofpropagation material, in particular in the case of seeds, also byapplying one or more coats.

The active compounds can be converted to the customary formulations,such as solutions, emulsions, wettable powders, suspensions, powders,dusts, pastes, soluble powders, granules, suspension-emulsionconcentrates, natural and synthetic materials impregnated with activecompound and microencapsulations in polymeric substances.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is, liquid solvents, and/orsolid carriers, optionally with the use of surfactants, that isemulsifiers and/or dispersants, and/or foam-formers.

If the extender used is water, it is also possible to employ for exampleorganic solvents as auxiliary solvents. Essentially, suitable liquidsolvents are: aromatics such as xylene, toluene or alkylnaphthalenes,chlorinated aromatics or chlorinated aliphatic hydrocarbons such aschlorobenzenes, chloroethylenes or methylene chloride, aliphatichydrocarbons such as cyclohexane or paraffins, for example petroleumfractions, mineral and vegetable oils, alcohols such as butanol orglycol and also their ethers and esters, ketones such as acetone, methylethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polarsolvents such as dimethylformamide and dimethyl sulphoxide, and alsowater.

Suitable solid carriers are:

for example ammonium salts and ground natural minerals such as kaolins,clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceousearth, and ground synthetic minerals, such as highly disperse silica,alumina and silicates; suitable solid carriers for granules are: forexample crushed and fractionated natural rocks such as calcite, marble,pumice, sepiolite and dolomite, and also synthetic granules of inorganicand organic meals, and granules of organic material such as sawdust,coconut shells, maize cobs and tobacco stalks; suitable emulsifiersand/or foam-formers are: for example nonionic and anionic emulsifiers,such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcoholethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkylsulphates, arylsulphonates and also protein hydrolysates; suitabledispersants are: for example lignin-sulphite waste liquors andmethylcellulose.

Tackifiers such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, as well as naturalphospholipids such as cephalins and lecithins, and syntheticphospholipids, can be used in the formulations. Other possible additivesare mineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs,such as alizarin dyestuffs, azo dyestuffs and metal phthalocyaninedyestuffs, and trace nutrients such as salts of iron, manganese, boron,copper, cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95% by weight ofactive compound, preferably between 0.5 and 90%.

The active compounds according to the invention can be employed as suchor in their formulations as a mixture with known fungicides,bactericides, acaricides, nematicides or insecticides in order, forexample, to increase the activity spectrum or avoid the development ofresistance. In many cases synergistic effects are achieved, ie. theefficacy of the mixture is greater than the efficacy of the individualcomponents.

Suitable co-components in mixtures are, for example, the followingcompounds:

Fungicides:

aldimorph, ampropylfos, ampropylfos-potassium, andoprim, anilazine,azaconazole, azoxystrobin,

benalaxyl, benodanil, benomyl, benzamacril, benzamacryl-isobutyl,bialaphos, binapacryl, biphenyl, bitertanol, blasticidin-S,bromuconazole, bupirimate, buthiobate,

calcium polysulphide, capsimycin, captafol, captan, carbendazim,carboxin, carvon, quinomethionate, chlobenthiazone, chlorfenazole,chloroneb, chloropicrin, chlorothalonil, chlozolinate, clozylacon,cufraneb, cymoxanil, cyproconazole, cyprodinil, cyprofuram,

debacarb, dichlorophen, diclobutrazole, diclofluanid, diclomezine,dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph,diniconazole, diniconazole-M, dinocap, diphenylamine, dipyrithione,ditalimfos, dithianon, dodemorph, dodine, drazoxolon,

ediphenphos, epoxiconazole, etaconazole, ethirimol, etridiazole,

famoxadon, fenapanil, fenarimol, fenbuconazole, fenfuram, fenitropan,fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentinhydroxide, ferbam, ferimzone, fluazinam, flumetover, fluoromide,fluquinconazole, flurprimidol, flusilazole, flusulfamide, flutolanil,flutriafol, folpet, fosetyl-aluminium, fosetyl-sodium, fthalide,fuberidazole, furalaxyl, furametpyr, furcarbonil, furconazole,furconazole-cis, furmecyclox,

guazatine,

hexachlorobenzene, hexaconazole, hymexazole,

imazalil, imibenconazole, iminoctadine, iminoctadine albesilate,iminoctadine triacetate, iodocarb, ipconazole, iprobenfos (IBP),iprodione, irumamycin, isoprothiolane, isovaledione,

kasugamycin, kresoxim-methyl, copper preparations, such as: copperhydroxide, copper naphthenate, copper oxychloride, copper sulphate,copper oxide, oxine-copper and Bordeaux mixture,

mancopper, mancozeb, maneb, meferimzone, mepanipyrim, mepronil,metalaxyl, metconazole, methasulfocarb, methfuroxam, metiram,metomeclam, metsulfovax, mildiomycin, myclobutanil, myclozolin,

nickel dimethyldithiocarbamate, nitrothal-isopropyl, nuarimol,

ofurace, oxadixyl, oxamocarb, oxolinic acid, oxycarboxim, oxyfenthiin,

paclobutrazole, pefurazoate, penconazole, pencycuron, phosdiphen,picoxystrobin, pimaricin, piperalin, polyoxin, polyoxorim, probenazole,prochloraz, procymidone, propamocarb, propanosine-sodium, propiconazole,propineb, pyraclostrobin, pyrazophos, pyrifenox, pyrimethanil,pyroquilon, pyroxyfur,

quinconazole, quintozene (PCNB),

sulphur and sulphur preparations,

tebuconazole, tecloftalam, tecnazene, tetcyclacis, tetraconazole,thiabendazole, thicyofen, thifluzamide, thiophanate-methyl, thiram,tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol,triazbutil, triazoxide, trichlamide, tricyclazole, tridemorph,trifloxystrobin, triflumizole, triforine, triticonazole,

uniconazole,

validamycin A, vinclozolin, viniconazole,

zarilamide, zineb, ziram and also

Dagger G,

OK-8705,

OK-8801,

α-(1,1-dimethylethyl)-β-(2-phenoxyethyl)-1H-1,2,4-triazole-1-ethanol,

α-(2,4-dichlorophenyl)-β-fluoro-β-propyl-1H-1,2,4-triazole-1-ethanol,

α-(2,4-dichlorophenyl)-β-methoxy-α-methyl-1H-1,2,4-triazole-1-ethanol,

α-(5-methyl-1,3-dioxan-5-yl)-β-[[4-(trifluoromethyl)-phenyl]-methylene]-1H-1,2,4-triazole-1-ethanol,

(5RS,6RS)-6-hydroxy-2,2,7,7-tetramethyl-5-(1H-1,2,4-triazol-1-yl)-3-octanone,

(E)-α-(methoxyimino)-N-methyl-2-phenoxy-phenylacetamide,

1-isopropyl{2-methyl-1-[[[1-(4-methylphenyl)-ethyl]-amino]-carbonyl]-propyl}-carbamate,

1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-ethanone-O-(phenylmethyl)-oxime,

1-(2-methyl-1-naphthalenyl)-1H-pyrrol-2,5-dione,

1-(3,5-dichlorophenyl)-3-(2-propenyl)-2,5-pyrrolidindione,

1-[(diiodomethyl)-sulphonyl]-4-methylbenzene,

1-[[2-(2,4-dichlorophenyl)-1,3-dioxolan-2-yl]-methyl]-1H-imidazole,

1-[[2-(4-chlorophenyl)-3-phenyloxiranyl]-methyl]-1H-1,2,4-triazole,

1-[1-[2-[(2,4-dichlorophenyl)-methoxy]-phenyl]-ethenyl]-1H-imidazole,

1-methyl-5-nonyl-2-(phenylmethyl)-3-pyrrolidinole,

2′,6′-dibromo-2-methyl-4′-trifluoromethoxy-4′-trifluoromethyl-1,3-thiazole-5-carboxanilide,

2,2-dichloro-N-[1-(4-chlorophenyl)-ethyl]-1-ethyl-3-methyl-cyclopropanecarboxamide,

2,6-dichloro-5-(methylthio)-4-pyrimidinyl-thiocyanate,

2,6-dichloro-N-(4-trifluoromethylbenzyl)-benzamide,

2,6-dichloro-N-[[4-(trifluoromethyl)-phenyl]methyl]-benzamide,

2-(2,3,3-triiodo-2-propenyl)-2H-tetrazole,

2-[(1-methylethyl)-sulphonyl]-5-(trichloromethyl)-1,3,4-thiadiazole,

2-[[6-deoxy-4-O-(4-O-methyl-β-D-glycopyranosyl)-α-D-glucopyranosyl]-amino]-4-methoxy-1H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile,

2-aminobutane,

2-bromo-2-(bromomethyl)-pentanedinitrile,

2-chloro-N-(2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl)-3-pyridinecarboxamide,

2-chloro-N-(2,6-dimethylphenyl)-N-(isothiocyanatomethyl)-acetamide,

2-phenylphenol (OPP),

3,4-dichloro-1-[4-(difluoromethoxy)-phenyl]-1H-pyrrol-2,5-dione,

3,5-dichloro-N-[cyano[(1-methyl-2-propynyl)-oxy]-methyl]-benzamide,

3-(1,1-dimethylpropyl)-1-oxo-1H-indene-2-carbonitrile,

3-[2-(4-chlorophenyl)-5-ethoxy-3-isoxazolidinyl]-pyridine,

4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulphonamide,

4-methyltetrazolo[1,5-a]quinazolin-5(4H)-one,

8-(1,1-dimethylethyl)-N-ethyl-N-propyl-1,4-dioxaspiro[4.5]decane-2-methanamine,

8-hydroxyquinoline sulphate,

9H-xanthene-2-[(phenylamino)-carbonyl]-9-carboxylic hydrazide,

bis-(1-methylethyl)-3-methyl-4-[(3-methylbenzoyl)-oxy]-2,5-thiophenedicarboxylate,

cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-cycloheptanol,

cis-4-[3-[4-(1,1-dimethylpropyl)-phenyl-2-methylpropyl]-2,6-dimethylmorpholinehydrochloride,

ethyl[(4-chlorophenyl)-azo]-cyanoacetate,

potassium bicarbonate,

methanetetrathiol-sodium salt,

methyl1-(2,3-dihydro-2,2-dimethyl-1H-inden-1-yl)-1H-imidazole-5-carboxylate,

methyl N-(2,6-dimethylphenyl)-N-(5-isoxazolylcarbonyl)-DL-alaninate,

methyl N-(chloroacetyl)-N-(2,6-dimethylphenyl)-DL-alaninate,

N-(2,3-dichloro-4-hydroxyphenyl)-1-methyl-cyclohexanecarboxamide,

N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-furanyl)-acetamide,

N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-thienyl)-acetamide,

N-(2-chloro-4-nitrophenyl)-4-methyl-3-nitrobenzenesulphonamide,

N-(4-cyclohexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidinamine,

N-(4-hexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidinamine,

N-(5-chloro-2-methylphenyl)-2-methoxy-N-(2-oxo-3-oxazolidinyl)-acetamide,

N-(6-methoxy)-3-pyridinyl-cyclopropanecarboxamide,

N-[2,2,2-trichloro-1-[(chloroacetyl)-amino]ethyl]-benzamide,

N-[3-chloro-4,5-bis(2-propinyloxy)-phenyl]-N′-methoxymethanimidamide,

N-formyl-N-hydroxy-DL-alanine-sodium salt,

O,O-diethyl[2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioate,

O-methyl S-phenyl phenylpropylphosphoramidothioate,

S-methyl 1,2,3-benzothiadiazole-7-carbothioate,

spiro[2H]-1-benzopyrane-2,1′(3′H)-isobenzofuran]-3′-one,

4-[3,4-dimethoxyphenyl)-3-(4-fluorophenyl)-acryloyl]-morpholine

Bactericides:

bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate,kasugamycin, octhilinone, furancarboxylic acid, oxytetracyclin,probenazole, streptomycin, tecloftalam, copper sulphate and other copperpreparations.

Insecticides/Acaricides/Nematicides:

abamectin, acephate, acetamiprid, acrinathrin, alanycarb, aldicarb,aldoxycarb, alpha-cypermethrin, alphamethrin, amitraz, avermectin, AZ60541, azadirachtin, azamethiphos, azinphos A, azinphos M, azocyclotin,

Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis, Bacillusthuringiensis, baculoviruses, Beauveria bassiana, Beauveria tenella,bendiocarb, benfuracarb, bensultap, benzoximate, betacyfluthrin,bifenazate, bifenthrin, bioethanomethrin, biopermethrin, bistrifluron,BPMC, bromophos A, bufencarb, buprofezin, butathiofos, butocarboxim,butylpyridaben,

cadusafos, carbaryl, carbofuran, carbophenothion, carbosulfan, cartap,chloethocarb, chlorethoxyfos, chlorfenapyr, chlorfenvinphos,chlorfluazuron, chlormephos, chlorpyrifos, chlorpyrifos M,chlovaporthrin, chromafenozide, cis-resmethrin, cispermethrin,clocythrin, cloethocarb, clofentezine, clothianidine, cyanophos,cycloprene, cycloprothrin, cyfluthrin, cyhalothrin, cyhexatin,cypermethrin, cyromazine,

deltamethrin, demeton M, demeton S, demeton-S-methyl, diafenthiuron,diazinon, dichlorvos, dicofol, diflubenzuron, dimethoate,dimethylvinphos, dinetofuran, diofenolan, disulfoton, docusat-sodium,dofenapyn,

eflusilanate, emamectin, empenthrin, endosulfan, Entomopfthora spp.,esfenvalerate, ethiofencarb, ethion, ethiprole, ethoprophos, etofenprox,etoxazole, etrimfos,

fenamiphos, fenazaquin, fenbutatin oxide, fenitrothion, fenothiocarb,fenoxacrim, fenoxycarb, fenpropathrin, fenpyrad, fenpyrithrin,fenpyroximate, fenthion, fenvalerate, fipronil, fluazinam, fluazuron,flubrocythrinate, flucycloxuron, flucythrinate, flufenoxuron,flumethrin, flupyrazofos, flutenzine, fluvalinate, fonophos,fosmethilan, fosthiazate, fubfenprox, furathiocarb,

granulosis viruses,

halofenozide, HCH, heptenophos, hexaflumuron, hexythiazox, hydroprene,

imidacloprid, indoxacarb, isazofos, isofenphos, isoxathion, ivermectin,

nuclear polyhedrosis viruses,

lambda-cyhalothrin, lufenuron,

malathion, mecarbam, metaldehyde, methamidophos, Metharhiziurnanisopliae, metharhizium flavoviride, methidathion, methiocarb,methoprene, methomyl, methoxyfenozide, metolcarb, metoxadiazone,mevinphos, milbemectin, milbemycin, monocrotophos,

naled, nitenpyram, nithiazine, novaluron,

omethoate, oxamyl, oxydemethon M,

Paecilomyces fumosoroseus, parathion A, parathion M, permethrin,phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim,pirimicarb, pirimiphos A, pirimiphos M, profenofos, promecarb,propargite, propoxur, prothiofos, prothoate, pymetrozine, pyraclofos,pyresmethrin, pyrethrum, pyridaben, pyridathion, pyrimidifen,pyriproxyfen,

quinalphos,

ribavirin,

salithion, sebufos, silafluofen, spinosad, spirodiclofen, sulfotep,sulprofos,

tau-fluvalinate, tebufenozide, tebufenpyrad, tebupirimiphos,teflubenzuron, tefluthrin, temephos, temivinphos, terbufos,tetrachlorvinphos, tetradifon, theta-cypermethrin, thiacloprid,thiamethoxam, thiapronil, thiatriphos, thiocyclam hydrogen oxalate,thiodicarb, thiofanox, thuringiensin, tralocythrin, tralomethrin,triarathene, triazamate, triazophos, triazuron, trichlophenidine,trichlorfon, triflumuron, trimethacarb,

vamidothion, vaniliprole, Verticillium lecanii,

YI 5302,

zeta-cypermethrin, zolaprofos,

(1R-cis)-[5-(phenylmethyl)-3-furanyl]-methyl-3-[(dihydro-2-oxo-3(2H)-furanylidene)-methyl]-2,2-dimethylcyclopropanecarboxylate,

(3-phenoxyphenyl)-methyl-2,2,3,3-tetramethylcyclopropanecarboxylate,

1-[(2-chloro-5-thiazolyl)methyl]tetrahydro-3,5-dimethyl-N-nitro-1,3,5-triazine-2(1H)-imine,

2-(2-chloro-6-fluorophenyl)-4-[4-(1,1-dimethylethyl)phenyl]-4,5-dihydro-oxazole,

2-(acetyloxy)-3-dodecyl-1,4-naphthalenedione,

2-chloro-N-[[[4-(1-phenylethoxy)-phenyl]-amino]-carbonyl]-benzamide,

2-chloro-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)-phenyl]-amino]-carbonyl]-benzamide,

3-methylphenyl propylcarbamate,

4-[4-(4-ethoxyphenyl)-4-methylpentyl]-1-fluoro-2-phenoxybenzene,

4-chloro-2-(1,1-dimethylethyl)-5-[[2-(2,6-dimethyl-4-phenoxyphenoxy)ethyl]thio]-3(2H)-pyridazinone,

4-chloro-2-(2-chloro-2-methylpropyl)-5-[(6-iodo-3-pyridinyl)methoxy]-3(2H)-pyridazinone,

4-chloro-5-[(6-chloro-3-pyridinyl)methoxy]-2-(3,4-dichlorophenyl)-3(2H)-pyridazinone,

Bacillus thuringiensis strain EG-2348,

[2-benzoyl-1-(1,1-dimethylethyl)-hydrazinobenzoic acid,

2,2-dimethyl-3-(2,4-dichlorophenyl)-2-oxo-1-oxaspiro[4.5]dec-3-en-4-ylbutanoate,

[3-[(6-chloro-3-pyridinyl)methyl]-2-thiazolidinylidene]-cyanamide,

dihydro-2-(nitromethylene)-2H-1,3-thiazine-3(4H)-carboxaldehyde,

ethyl[2-[[1,6-dihydro-6-oxo-1-(phenylmethyl)-4-pyridazinyl]oxy]ethyl]carbamate,

N-(3,4,4-trifluoro-1-oxo-3-butenyl)-glycine,

N-(4-chlorophenyl)-3-[4-(difluoromethoxy)phenyl]-4,5-dihydro-4-phenyl-1H-pyrazole-1-carboxamide,

N-[(2-chloro-5-thiazolyl)methyl]-N′-methyl-N″-nitro-guanidine,

N-methyl-N′-(1-methyl-2-propenyl)-1,2-hydrazinedicarbothioamide,

N-methyl-N′-2-propenyl-1,2-hydrazinedicarbothioamide,

O,O-diethyl-[2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioate,

N-cyanomethyl-4-trifluoromethyl-nicotinamide,

3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-[3-(5-trifluoromethylpyridin-2-yloxy)-propoxy]-benzene.

It is also possible to admix other known active compounds, such asherbicides, fertilizers and growth regulators, or safeners orsemiochemicals.

When used as insecticides, the active compounds according to theinvention can furthermore be present in their commercially availableformulations and in the use forms, prepared from these formulations, asa mixture with synergistic agents. Synergistic agents are compoundswhich increase the action of the active compounds, without it beingnecessary for the synergistic agent added to be active itself.

When used as insecticides, the active compounds according to theinvention can furthermore be present in their commercially availableformulations and in the use forms, prepared from these formulations, asa mixture with inhibitors which reduce the degradation of the activecompound after use in the vicinity of the plant, on the surface of partsof plants or in plant tissue.

The active compound content of the use forms prepared from thecommercially available formulations can vary within wide limits. Theactive compound concentration of the use forms can be from 0.0000001 to95% by weight of active compound, preferably between 0.0001 and 1% byweight.

The compounds are employed in a customary manner appropriate for the useforms.

When used against hygiene pests and pests of stored products, the activecompound is distinguished by an excellent residual action on wood andclay as well as by a good stability to alkali on limed substrates.

As already mentioned above, it is possible to treat all plants and theirparts according to the invention. In a preferred embodiment, wild plantspecies and plant cultivars, or those obtained by conventionalbiological breeding, such as crossing or protoplast fusion, and partsthereof, are treated. In a further preferred embodiment, transgenicplants and plant cultivars obtained by genetic engineering, ifappropriate in combination with conventional methods (GeneticallyModified Organisms), and parts thereof are treated. The term “parts” or“parts of plants” or “plant parts” has been explained above.

Particularly preferably, plants of the plant cultivars which are in eachcase commercially available or in use are treated according to theinvention. Plant cultivars are understood as meaning plants with novelproperties (“traits”) which are grown by conventional cultivation, bymutagenesis or by recombinant DNA techniques. These may be cultivars,biotypes or genotypes.

Depending on the plant species or plant cultivars, their location andgrowth conditions (soils, climate, vegetation period, diet), thetreatment according to the invention may also result in superadditive(“synergistic”) effects. Thus, for example, reduced application ratesand/or a widening of the activity spectrum and/or an increase in theactivity of the substances and compositions to be used according to theinvention, better plant growth, increased tolerance to high or lowtemperatures, increased tolerance to drought or to water or soil saltcontent, increased flowering performance, easier harvesting, acceleratedmaturation, higher harvest yields, better quality and/or a highernutritional value of the harvested products, better storage stabilityand/or processability of the harvested products are possible whichexceed the effects which were actually to be expected.

The transgenic plants or plant cultivars (i.e. those obtained by geneticengineering) which are preferably to be treated according to theinvention include all plants which, in the genetic modification,received genetic material which imparts particularly advantageous usefulproperties (“traits”) to these plants. Examples of such properties arebetter plant growth, increased tolerance to high or low temperatures,increased tolerance to drought or to water or soil salt content,increased flowering performance, easier harvesting, acceleratedmaturation, higher harvest yields, better quality and/or a highernutritional value of the harvested products, better storage stabilityand/or processability of the harvested products. Further andparticularly emphasized examples of such properties are a better defenseof the plants against animal and microbial pests, such as againstinsects, mites, phytopathogenic fungi, bacteria and/or viruses, and alsoincreased tolerance of the plants to certain herbicidally activecompounds. Examples of transgenic plants which may be mentioned are theimportant crop plants, such as cereals (wheat, rice), maize, soya beans,potatoes, cotton, tobacco, oilseed rape and also fruit plants (with thefruits apples, pears, citrus fruits and grapes), and particular emphasisis given to maize, soya beans, potatoes, cotton, tobacco and oilseedrape. Traits that are emphasized are in particular increased defense ofthe plants against insects arachnids, nematodes and slugs and snails bytoxins formed in the plants, in particular those formed in the plants bythe genetic material from Bacillus thuringiensis (for example by thegenes CryIA(a), CryIA(b), CryIA(c), CryIIA, CryIIIA, CryIIIB2, Cry9cCry2Ab, Cry3Bb and CryIF and also combinations thereof) (hereinbelowreferred to as “Bt plants”). Traits which are also particularlyemphasized are the increased resistance of plants to fungi, bacteria andviruses by systemic acquired resistance (SAR), systemin, phytoalexins,elicitors and resistance genes and the correspondingly expressedproteins and toxins. Traits that are furthermore particularly emphasizedare the increased tolerance of the plants to certain herbicidally activecompounds, for example imidazolinones, sulphonylureas, glyphosate orphosphinotricin (for example the “PAT” gene). The genes which impart thedesired traits in question can also be present in combination with oneanother in the transgenic plants. Examples of “Bt plants” which may bementioned are maize varieties, cotton varieties, soya bean varieties andpotato varieties which are sold under the trade names YIELD GARD® (forexample maize, cotton, soya beans), KnockOut® (for example maize),StarLink® (for example maize), Bollgard® (cotton), Nucotn® (cotton) andNewLeaf® (potato). Examples of herbicide-tolerant plants which may bementioned are maize varieties, cotton varieties and soya bean varietieswhich are sold under the trade names Roundup Ready® (tolerance toglyphosate, for example maize, cotton, soya bean), Liberty Link®(tolerance to phosphinotricin, for example oilseed rape), IMI®(tolerance to imidazolinones) and STS® (tolerance to sulphonylureas, forexample maize). Herbicide-resistant plants (plants bred in aconventional manner for herbicide tolerance) which may be mentionedinclude the varieties sold under the name Clearfield® (for examplemaize). Of course, these statements also apply to plant cultivars havingthese genetic traits or genetic traits still to be developed, whichcultivars will be developed and/or marketed in the future.

The plants listed can be treated according to the invention in aparticularly advantageous manner with the compounds of the formula I orthe active compound mixtures according to the invention. The preferredranges stated above for the active compounds or mixtures also apply tothe treatment of these plants. Particular emphasis is given to thetreatment of plants with the compounds or mixtures specificallymentioned in the present text.

The active compounds according to the invention act not only againstplant, hygiene and stored product pests, but also in the veterinarymedicine sector against animal parasites (ectoparasites), such as hardticks, soft ticks, mange mites, harvest mites, flies (biting andlicking), parasitic fly larvae, lice, hair lice, feather lice and fleas.These parasites include:

From the order of the Anoplurida, for example, Haematopinus spp.,Linognathus spp., Pediculus spp., Phtirus spp. and Solenopotes spp.

From the order of the Mallophagida and the suborders Amblycerina andIschnocerina, for example, Trimenopon spp., Menopon spp., Trinoton spp.,Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp.,Trichodectes spp. and Felicola spp.

From the order of the Diptera and the suborders Nematocerina andBrachycerina, for example, Aedes spp., Anopheles spp., Culex spp.,Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp.,Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus sp., Tabanusspp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp.,Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fanniaspp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp.,Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp.,Gasterophilus spp., Hippobosca spp., Lipoptena spp. and Melophagus spp.

From the order of the Siphonapterida, for example Pulex spp.,Ctenocephalides spp., Xenopsylla spp. and Ceratophyllus spp.

From the order of the Heteropterida, for example, Cimex spp., Triatomaspp., Rhodnius spp. and Panstrongylus spp.

From the order of the Blattarida, for example Blatta orientalis,Periplaneta americana, Blattela germanica and Supella spp.

From the subclass of the Acaria (Acarina) and the orders of the Meta-and Mesostigmata, for example, Argas spp., Ornithodorus spp., Otobiusspp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp.,Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp.,Raillietia spp., Pneumonyssus spp., Sternostoma spp. and Varroa spp.

From the order of the Actinedida (Prostigmata) and Acaridida(Astigmata), for example, Acarapis spp., Cheyletiella spp.,Ornithochejiletia spp., Myobia spp., Psorergates spp., Demodex spp.,Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp.,Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp.,Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp.,Knemidocoptes spp., Cytodites spp. and Laminosioptes spp.

The active compounds of the formula (1) according to the invention arealso suitable for controlling arthropods which infest agriculturalproductive livestock, such as, for example, cattle, sheep, goats,horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys,ducks, geese and bees, other pets, such as, for example, dogs, cats,caged birds and aquarium fish, and also so-called test animals, such as,for example, hamsters, guinea pigs, rats and mice. By controlling thesearthropods, cases of death and reduction in productivity (for meat,milk, wool, hides, eggs, honey etc.) should be diminished, so that moreeconomic and easier animal husbandry is possible by use of the activecompounds according to the invention.

The active compounds according to the invention are used in theveterinary sector in a known manner by enteral administration in theform of, for example, tablets, capsules, potions, drenches, granules,pastes, boluses, the feed-through process and suppositories, byparenteral administration, such as, for example, by injection(intramuscular, subcutaneous, intravenous, intraperitoneal and thelike), implants, by nasal administration, by dermal use in the form, forexample, of dipping or bathing, spraying, pouring on and spotting on,washing and powdering, and also with the aid of moulded articlescontaining the active compound, such as collars, ear marks, tail marks,limb bands, halters, marking devices and the like.

When used for cattle, poultry, pets and the like, the active compoundsof the formula (I) can be used as formulations (for example powders,emulsions, free-flowing compositions), which comprise the activecompounds in an amount of 1 to 80% by weight, directly or after 100 to10 000-fold dilution, or they can be used as a chemical bath.

It has furthermore been found that the compounds according to theinvention have a strong insecticidal action against insects whichdestroy industrial materials.

The following insects may be mentioned as examples and as preferred—butwithout limitation:

Beetles, such as

Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobiumrufovillosum, Ptilinus pecticornis, Dendrobium pertinex, Ernobiusmollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctusplanicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon aequale,Minthes rugicollis, Xyleborus spec. Tryptodendron spec. Apate monachus,Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec.Dinoderus minutus.

Hymenopterons, such as

Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur.

Termites, such as

Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola,Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermeslucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis,Coptotermes formosanus.

Bristletails, such as Lepisma saccharina.

Industrial materials in the present connection are to be understood asmeaning non-living materials, such as, preferably, plastics, adhesives,sizes, paper and card, leather, wood and processed wood products andcoating compositions.

Wood and processed wood products are materials to be protected,especially preferably, from insect infestation.

Wood and processed wood products which can be protected by the agentsaccording to the invention or mixtures comprising these are to beunderstood as meaning, for example:

building timber, wooden beams, railway sleepers, bridge components, boatjetties, wooden vehicles, boxes, pallets, containers, telegraph poles,wood panelling, wooden windows and doors, plywood, chipboard, joinery orwooden products which are used quite generally in house-building or inbuilding joinery.

The active compounds can be used as such, in the form of concentrates orgenerally customary formulations, such as powders, granules, solutions,suspensions, emulsions or pastes.

The formulations mentioned can be prepared in a manner known per se, forexample by mixing the active compounds with at least one solvent ordiluent, emulsifier, dispersing agent and/or binder or fixing agent, awater repellent, if appropriate siccatives and UV stabilizers and ifappropriate dyestuffs and pigments, and also other processingauxiliaries.

The insecticidal compositions or concentrates used for the preservationof wood and wood-derived timber products comprise the active compoundaccording to the invention in a concentration of 0.0001 to 95% byweight, in particular 0.001 to 60% by weight.

The amount of the compositions or concentrates employed depends on thenature and occurrence of the insects and on the medium. The optimumamount employed can be determined for the use in each case by a seriesof tests. In general, however, it is sufficient to employ 0.0001 to 20%by weight, preferably 0.001 to 10% by weight, of the active compound,based on the material to be preserved.

Solvents and/or diluents which are used are an organic-chemical solventor solvent mixture and/or an oily or oil-like organic-chemical solventor solvent mixture of low volatility and/or a polar organic-chemicalsolvent or solvent mixture and/or water, and if appropriate anemulsifier and/or wetting agent.

Organic-chemical solvents which are preferably used are oily or oil-likesolvents having an evaporation number above 35 and a flashpoint above30° C., preferably above 45° C. Substances which are used as such oilyor oil-like water-insoluble solvents of low volatility are appropriatemineral oils or aromatic fractions thereof, or solvent mixturescontaining mineral oils, preferably white spirit, petroleum and/oralkylbenzene.

Mineral oils having a boiling range from 170 to 220° C., white spirithaving a boiling range from 170 to 220° C., spindle oil having a boilingrange from 250 to 350° C., petroleum and aromatics having a boilingrange from 160 to 280° C., terpentine oil and the like, areadvantageously employed.

In a preferred embodiment, liquid aliphatic hydrocarbons having aboiling range from 180 to 210° C. or high-boiling mixtures of aromaticand aliphatic hydrocarbons having a boiling range from 180 to 220° C.and/or spindle oil and/or monochloronaphthalene, preferablyα-monochloronaphthalene, are used.

The organic oily or oil-like solvents of low volatility which have anevaporation number above 35 and a flashpoint above 30° C., preferablyabove 45° C., can be replaced in part by organic-chemical solvents ofhigh or medium volatility, providing that the solvent mixture likewisehas an evaporation number above 35 and a flashpoint above 30° C.,preferably above 45° C., and that the insecticide/fungicide mixture issoluble or emulsifiable in this solvent mixture.

According to a preferred embodiment, some of the organic-chemicalsolvent or solvent mixture or an aliphatic polar organic-chemicalsolvent or solvent mixture is replaced. Aliphatic organic-chemicalsolvents containing hydroxyl and/or ester and/or ether groups, such as,for example, glycol ethers, esters or the like, are preferably used.

Organic-chemical binders which are used in the context of the presentinvention are the synthetic resins and/or binding drying oils which areknown per se, are water-dilutable and/or are soluble or dispersible oremulsifiable in the organic-chemical solvents employed, in particularbinders consisting of or comprising an acrylate resin, a vinyl resin,for example polyvinyl acetate, polyester resin, polycondensation orpolyaddition resin, polyurethane resin, alkyd resin or modified alkydresin, phenolic resin, hydrocarbon resin, such as indene-cumarone resin,silicone resin, drying vegetable oils and/or drying oils and/orphysically drying binders based on a natural and/or synthetic resin.

The synthetic resin used as the binder can be employed in the form of anemulsion, dispersion or solution. Bitumen or bituminous substances canalso be used as binders in an amount of up to 10% by weight. Dyestuffs,pigments, water-repelling agents, odour correctants and inhibitors oranticorrosive agents and the like which are known per se canadditionally be employed.

It is preferred according to the invention for the composition orconcentrate to comprise, as the organic-chemical binder, at least onealkyd resin or modified alkyd resin and/or one drying vegetable oil.Alkyd resins having an oil content of more than 45% by weight,preferably 50 to 68% by weight, are preferably used according to theinvention.

All or some of the binder mentioned can be replaced by a fixing agent(mixture) or a plasticizer (mixture). These additives are intended toprevent evaporation of the active compounds and crystallization orprecipitation. They preferably replace 0.01 to 30% of the binder (basedon 100% of the binder employed).

The plasticizers originate from the chemical classes of phthalic acidesters, such as dibutyl, dioctyl or benzyl butyl phthalate, phosphoricacid esters, such as tributyl phosphate, adipic acid esters, such asdi-(2-ethylhexyl)adipate, stearates, such as butyl stearate or amylstearate, oleates, such as butyl oleate, glycerol ethers or highermolecular weight glycol ethers, glycerol esters and p-toluenesulphonicacid esters.

Fixing agents are based chemically on polyvinyl alkyl ethers, such as,for example, polyvinyl methyl ether or ketones, such as benzophenone orethylenebenzophenone.

Possible solvents or diluents are, in particular, also water, ifappropriate as a mixture with one or more of the abovementionedorganic-chemical solvents or diluents, emulsifiers and dispersingagents.

Particularly effective preservation of wood is achieved by impregnationprocesses on a large industrial scale, for example vacuum, double vacuumor pressure processes.

The ready-to-use compositions can also comprise other insecticides, ifappropriate, and also one or more fungicides, if appropriate.

Possible additional mixing partners are, preferably, the insecticidesand fungicides mentioned in WO 94/29 268. The compounds mentioned inthis document are an explicit constituent of the present application.

Especially preferred mixing partners which may be mentioned areinsecticides, such as chlorpyriphos, phoxim, silafluofin, alphamethrin,cyfluthrin, cypermethrin, deltamethrin, permethrin, imidacloprid, NI-25,flufenoxuron, hexaflumuron, transfluthrin, thiacloprid,methoxyphenoxide, triflumuron, chlothianidin, spinosad and tefluthrin,

and also fungicides, such as epoxyconazole, hexaconazole, azaconazole,propiconazole, tebuconazole, cyproconazole, metconazole, imazalil,dichlorfluanid, tolylfluanid, 3-iodo-2-propinyl-butylcarbamate,N-octyl-isothiazolin-3-one and 4,5-dichloro-N-octyl isothiazol in-3-one.

The compounds according to the invention can at the same time beemployed for protecting objects which come into contact with saltwateror brackish water, such as hulls, screens, nets, buildings, moorings andsignalling systems, against fouling.

Fouling by sessile Oligochaeta, such as Serpulidae, and by shells andspecies from the Ledamorpha group (goose barnacles), such as variousLepas and Scalpellum species, or by species from the Balanomorpha group(acorn barnacles), such as Balanus or Pollicipes species, increases thefrictional drag of ships and, as a consequence, leads to a markedincrease in operation costs owing to higher energy consumption andadditionally frequent residence in the dry dock.

Apart from fouling by algae, for example Ectocarpus sp. and Ceramiumsp., in particular fouling by sessile Entomostraka groups, which comeunder the generic term Cirripedia (cirriped crustaceans), is ofparticular importance.

Surprisingly, it has now been found that the compounds according to theinvention, alone or in combination with other active compounds, have anoutstanding antifouling action.

Using the compounds according to the invention, alone or in combinationwith other active compounds, allows the use of heavy metals such as, forexample, in bis(trialkyltin)sulphides, tri-n-butyltin laurate,tri-n-butyltin chloride, copper(I) oxide, triethyltin chloride,tri-n-butyl(2-phenyl-4-chlorophenoxy)tin, tributyltin oxide, molybdenumdisulphide, antimony oxide, polymeric butyl titanate,phenyl(bispyridine)bismuth chloride, tri-n-butyltin fluoride, manganeseethylenebisthiocarbamate, zinc dimethyldithiocarbamate, zincethylenebisthiocarbamate, zinc salts and copper salts of 2-pyridinethiol1-oxide, bisdimethyldithiocarbamoylzinc ethylenebisthiocarbamate, zincoxide, copper(I) ethylenebisdithiocarbamate, copper thiocyanate, coppernaphthenate and tributyltin halides to be dispensed with, or theconcentration of these compounds to be substantially reduced.

If appropriate, the ready-to-use antifouling paints can additionallycomprise other active compounds, preferably algicides, fungicides,herbicides, molluscicides, or other antifouling active compounds.

Preferably suitable components in combinations with the antifoulingcompositions according to the invention are:

algicides such as

2-tert-butylamino-4-cyclopropylamino-6-methylthio-1,3,5-triazine,dichlorophen, diuron, endothal, fentin acetate, isoproturon,methabenzthiazuron, oxyfluorfen, quinoclamine and terbutryn;

fungicides such as

benzo[b]thiophenecarboxylic acid cyclohexylamide S,S-dioxide,dichlofluanid, fluorfolpet, 3-iodo-2-propinyl butylcarbamate,tolylfluanid and azoles such as azaconazole, cyproconazole,epoxyconazole, hexaconazole, metconazole, propiconazole andtebuconazole;

molluscicides such as

fentin acetate, metaldehyde, methiocarb, niclosamid, thiodicarb andtrimethacarb fechelate;

or conventional antifouling active compounds such as

4,5-dichloro-2-octyl-4-isothiazolin-3-one, diiodomethylparatrylsulphone, 2-(N,N-dimethylthiocarbamoylthio)-5-nitrothiazyl, potassium,copper, sodium and zinc salts of 2-pyridinethiol 1-oxide,pyridinetriphenylborane, tetrabutyldistannoxane,2,3,5,6-tetrachloro-4-(methylsulphonyl)-pyridine,2,4,5,6-tetrachloroisophthalonitrile, tetramethylthiuram disulphide and2,4,6-trichlorophenylmaleiimide.

The antifouling compositions used comprise the active compound accordingto the invention of the compounds according to the invention in aconcentration of 0.001 to 50% by weight, in particular 0.01 to 20% byweight.

Moreover, the antifouling compositions according to the inventioncomprise the customary components such as, for example, those describedin Ungerer, Chem. Ind. 1985, 37, 730-732 and Williams, AntifoulingMarine Coatings, Noyes, Park Ridge, 1973.

Besides the algicidal, fungicidal, molluscicidal active compounds andinsecticidal active compounds according to the invention, antifoulingpaints comprise, in particular, binders.

Examples of recognized binders are polyvinyl chloride in a solventsystem, chlorinated rubber in a solvent system, acrylic resins in asolvent system, in particular in an aqueous system, vinyl chloride/vinylacetate copolymer systems in the form of aqueous dispersions or in theform of organic solvent systems, butadiene/styrene/acrylonitrilerubbers, drying oils such as linseed oil, resin esters or modifiedhardened resins in combination with tar or bitumens, asphalt and epoxycompounds, small amounts of chlorine rubber, chlorinated polypropyleneand vinyl resins.

If appropriate, paints also comprise inorganic pigments, organicpigments or colorants which are preferably insoluble in salt water.Paints may furthermore comprise materials such as colophonium to allowcontrolled release of the active compounds. Furthermore, the paints maycomprise plasticizers, modifiers which affect the rheological propertiesand other conventional constituents. The compounds according to theinvention or the abovementioned mixtures may also be incorporated intoself-polishing antifouling systems.

The active compounds are also suitable for controlling animal pests, inparticular insects, arachnids and mites, which are found in enclosedspaces such as, for example, dwellings, factory halls, offices, vehiclecabins and the like. They can be employed alone or in combination withother active compounds and auxiliaries in domestic insecticide productsfor controlling these pests. They are active against sensitive andresistant species and against all developmental stages. These pestsinclude:

From the order of the Scorpionidea, for example, Buthus occitanus.

From the order of the Acarina, for example, Argas persicus, Argasreflexus, Bryobia ssp., Dermanyssus gallinae, Glyciphagus domesticus,Ornithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi,Neutrombicula autumnalis, Dermatophagoides pteronissimus,Dermatophagoides forinae.

From the order of the Araneae, for example, Aviculariidae, Arsenide.

From the order of the Opiliones, for example, Pseudoscorpiones chelifer,Pseudoscorpiones cheiridium, Opiliones phalangium.

From the order of the Isopoda, for example, Oniscus asellus, Porcellioscaber.

From the order of the Diplopoda, for example, Blaniulus guttulatus,Polydesmus spp.

From the order of the Chilopoda, for example, Geophilus spp.

From the order of the Zygentoma, for example, Ctenolepisma spp., Lepismasaccharina, Lepismodes inquilinus.

From the order of the Blattaria, for example, Blatta orientalies,Blattella germanica, Blattella asahinai, Leucophaea maderae, Panchloraspp., Parcoblatta spp., Periplaneta australasiae, Periplaneta americana,Periplaneta brunnea, Periplaneta fuliginosa, Supella longipalpa.

From the order of the Saltatoria, for example, Acheta domesticus.

From the order of the Dermaptera, for example, Forficula auricularia.

From the order of the Isoptera, for example, Kalotermes spp.,Reticulitermes spp.

From the order of the Psocoptera, for example, Lepinatus spp.,Liposcelis spp.

From the order of the Coleptera, for example, Anthrenus spp., Attagenusspp., Dermestes spp., Latheticus oryzae, Necrobia spp., Ptinus spp.,Rhizopertha dominica, Sitophilus granarius, Sitophilus oryzae,Sitophilus zeamais, Stegobium paniceum.

From the order of the Diptera, for example, Aedes aegypti, Aedesalbopictus, Aedes taeniorhynchus, Anopheles spp., Calliphoraerythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culexpipiens, Culex tarsalis, Drosophila spp., Fannia canicularis, Muscadomestica, Phlebotomus spp., Sarcophaga carnaria, Simulium spp.,Stomoxys calcitrans, Tipula paludosa.

From the order of the Lepidoptera, for example, Achroia grisella,Galleria mellonella, Plodia interpunctella, Tinea cloacella, Tineapellionella, Tineola bisselliella.

From the order of the Siphonaptera, for example, Ctenocephalides canis,Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsyllacheopis.

From the order of the Hymenoptera, for example, Camponotus herculeanus,Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis,Paravespula spp., Tetramorium caespitum.

From the order of the Anoplura, for example, Pediculus humanus capitis,Pediculus humanus corporis, Phthirus pubis.

From the order of the Heteroptera, for example, Cimex hemipterus, Cimexlectularius, Rhodinus prolixus, Triatoma infestans.

In the field of household insecticides, they are used alone or incombination with other suitable active compounds, such as phosphoricacid esters, carbamates, pyrethroids, neonicotinoides, growth regulatorsor active compounds from other known classes of insecticides.

They are used in aerosols, pressure-free spray products, for examplepump and atomizer sprays, automatic fogging systems, foggers, foams,gels, evaporator products with evaporator tablets made of cellulose orpolymer, liquid evaporators, gel and membrane evaporators,propeller-driven evaporators, energy-free or passive evaporationsystems, moth papers, moth bags and moth gels, as granules or dusts, inbaits for spreading or in bait stations.

The active compounds according to the invention can also be used asdefoliants, desiccants, haulm killers and, especially, as weedkillers.Weeds in the broadest sense are understood to mean all plants which growin locations where they are undesired. Whether the substances accordingto the invention act as total or selective herbicides dependsessentially on the amount used.

The active compounds according to the invention can be used, forexample, in connection with the following plants:

Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia,Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella, Carduus,Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium,Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus,Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha,Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum,Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola,Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea,Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola,Xanthium.

Dicotyledonous crops of the genera: Arachis, Beta, Brassica, Cucumis,Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca,Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia.

Monocotyledonous weeds of the genera: Aegilops, Agropyron, Agrostis,Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina,Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis,Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera,Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum,Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria,Sorghum.

Monocotyledonous crops of the genera: Allium, Ananas, Asparagus, Avena,Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale,Triticum, Zea.

However, the use of the active compounds according to the invention isin no way restricted to these genera, but also extends in the samemanner to other plants.

The active compounds according to the invention are suitable, dependingon the concentration, for the total control of weeds, for example onindustrial terrain and rail tracks, and on paths and areas with andwithout tree plantings. Similarly, the active compounds according to theinvention can be employed for controlling weeds in perennial crops, forexample forests, decorative tree plantings, orchards, vineyards, citrusgroves, nut orchards, banana plantations, coffee plantations, teaplantations, rubber plantations, oil palm plantations, cocoaplantations, soft fruit plantings and hop fields, on lawns, turf andpastureland, and for the selective control of weeds in annual crops.

The compounds of the formula (I) according to the invention have strongherbicidal activity and a broad activity spectrum when used on the soiland on above-ground parts of plants. To a certain extent they are alsosuitable for the selective control of monocotyledonous anddicotyledonous weeds in monocotyledonous and dicotyledonous crops, bothby the pre-emergence and by the post-emergence method.

At certain concentrations or application rates, the active compoundsaccording to the invention can also be employed for controlling animalpests and fungal or bacterial plant diseases. If appropriate, they canalso be used as intermediates or precursors for the synthesis of otheractive compounds.

The active compounds can be converted into the customary formulationssuch as solutions, emulsions, wettable powders, suspensions, powders,dusts, pastes, soluble powders, granules, suspension-emulsionconcentrates, natural and synthetic materials impregnated with activecompound, and microencapsulations in polymeric materials.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is, liquid solvents and/orsolid carriers, optionally with the use of surfactants, that is,emulsifiers and/or dispersants, and/or foam formers.

If the extender used is water, it is also possible to employ, forexample, organic solvents as auxiliary solvents. Essentially, suitableliquid solvents are: aromatics such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics and chlorinated aliphatichydrocarbons such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons such as cyclohexane or paraffins, forexample mineral oil fractions, mineral and vegetable oils, alcohols suchas butanol or glycol and their ethers and esters, ketones such asacetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone,strongly polar solvents such as dimethylformamide and dimethylsulphoxide, or else water.

Suitable solid carriers are: for example ammonium salts and groundnatural minerals such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticminerals such as finely divided silica, alumina and silicates; suitablesolid carriers for granules are: for example crushed and fractionatednatural rocks such as calcite, marble, pumice, sepiolite and dolomite,or else synthetic granules of inorganic and organic meals, and granulesof organic material such as sawdust, coconut shells, maize cobs andtobacco stalks; suitable emulsifiers and/or foam formers are: forexample nonionic and anionic emulsifiers such as polyoxyethylene fattyacid esters, polyoxyethylene fatty alcohol ethers, for example alkylarylpolyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates,or else protein hydrolysates; suitable dispersants are: for examplelignosulphite waste liquors and methylcellulose.

Tackifiers such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, or else naturalphospholipids such as cephalins and lecithins and syntheticphospholipids can be used in the formulations. Other possible additivesare mineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic colorants suchas alizarin colorants, azo colorants and metal phthalocyanine colorants,and trace nutrients such as salts of iron, manganese, boron, copper,cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95% by weight ofactive compound, preferably between 0.5 and 90%.

For controlling weeds, the active compounds according to the invention,as such or in their formulations, can also be used as mixtures withknown herbicides and/or substances which improve the compatibility withcrop plants (“safeners”), finished formulations or tank mixes beingpossible. Also possible are mixtures with weed-killers comprising one ormore known herbicides and a safener.

Possible components for the mixtures are known herbicides, for exampleacetochlor, acifluorfen (-sodium), aclonifen, alachlor, alloxydim(-sodium), ametryne, amicarbazone, amidochlor, amidosulfuron, anilofos,asulam, atrazine, azafenidin, azimsulfuron, beflubutamid, benazolin(-ethyl), benfuresate, bensulfuron (-methyl), bentazon, benzfendizone,benzobicyclon, benzofenap, benzoylprop (-ethyl), bialaphos, bifenox,bispyribac (-sodium), bromobutide, bromofenoxim, bromoxynil, butachlor,butafenacil (-allyl), butroxydim, butylate, cafenstrole, caloxydim,carbetamide, carfentrazone (-ethyl), chlomethoxyfen, chloramben,chloridazon, chlorimuron (-ethyl), chlornitrofen, chlorsulfuron,chlortoluron, cinidon (-ethyl), cinmethylin, cinosulfuron, clefoxydim,clethodim, clodinafop (-propargyl), clomazone, clomeprop, clopyralid,clopyrasulfuron (-methyl), cloransulam (-methyl), cumyluron, cyanazine,cybutryne, cycloate, cyclosulfamuron, cycloxydim, cyhalofop (-butyl),2,4-D, 2,4-DB, desmedipham, diallate, dicamba, dichlorprop (-P),diclofop (-methyl), diclosulam, diethatyl (-ethyl), difenzoquat,diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethachlor,dimethametryn, dimethenamid, dimexyflam, dinitramine, diphenamid,diquat, dithiopyr, diuron, dymron, epropodan, EPTC, esprocarb,ethalfluralin, ethametsulfuron (-methyl), ethofumesate, ethoxyfen,ethoxysulfuron, etobenzanid, fenoxaprop (-P-ethyl), fentrazamide,flamprop (-isopropyl, -isopropyl-L, -methyl), flazasulfuron, florasulam,fluazifop (-P-butyl), fluazolate, flucarbazone (-sodium), flufenacet,flumetsulam, flumiclorac (-pentyl), flumioxazin, flumipropyn,flumetsulam, fluometuron, fluorochloridone, fluoroglycofen (-ethyl),flupoxam, flupropacil, flurpyrsulfuron (-methyl, -sodium), flurenol(-butyl), fluridone, fluroxypyr (-butoxypropyl, -meptyl), flurprimidol,flurtamone, fluthiacet (-methyl), fluthiamide, fomesafen, foramsulfuron,glufosinate (-ammonium), glyphosate (-isopropylammonium), halosafen,haloxyfop (-ethoxyethyl, -P-methyl), hexazinone, imazamethabenz(-methyl), imazamethapyr, imazamox, imazapic, imazapyr, imazaquin,imazethapyr, imazosulfuron, iodosulfuron (-methyl, -sodium), ioxynil,isopropalin, isoproturon, isouron, isoxaben, isoxachlortole,isoxaflutole, isoxapyrifop, lactofen, lenacil, linuron, MCPA, mecoprop,mefenacet, mesotrione, metamitron, metazachlor, methabenzthiazuron,metobenzuron, metobromuron, (alpha-) metolachlor, metosulam, metoxuron,metribuzin, metsulfuron (-methyl), molinate, monolinuron, naproanilide,napropamide, neburon, nicosulfuron, norflurazon, orbencarb, oryzalin,oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen,paraquat, pelargonic acid, pendimethalin, pendralin, pentoxazone,phenmedipham, picolinafen, piperophos, pretilachlor, primisulfuron(-methyl), profluazol, prometryn, propachlor, propanil, propaquizafop,propisochlor, propoxycarbazone (-sodium), propyzamide, prosulfocarb,prosulfuron, pyraflufen (-ethyl), pyrazogyl, pyrazolate, pyrazosulfuron(-ethyl), pyrazoxyfen, pyribenzoxim, pyributicarb, pyridate, pyridatol,pyriftalid, pyriminobac (-methyl), pyrithiobac (-sodium), quinchlorac,quinmerac, quinoclamine, quizalofop (-P-ethyl, -P-tefuryl), rimsulfuron,sethoxydim, simazine, simetryn, sulcotrione, sulfentrazone, sulfometuron(-methyl), sulfosate, sulfosulfuron, tebutam, tebuthiuron, tepraloxydim,terbuthylazine, terbutryn, thenylchlor, thiafluamide, thiazopyr,thidiazimin, thifensulfuron (-methyl), thiobencarb, tiocarbazil,tralkoxydim, triallate, triasulfuron, tribenuron (-methyl), triclopyr,tridiphane, trifluralin, trifloxysulfuron, triflusulfuron (-methyl),tritosulfuron.

Furthermore suitable for the mixtures are known safeners, for example:AD-67, BAS-145138, benoxacor, cloquintocet (-mexyl), cyometrinil, 2,4-D,DKA-24, dichlormid, dymron, fenclorim, fenchlorazol (-ethyl), flurazole,fluxofenim, furilazole, isoxadifen (-ethyl), MCPA, mecoprop (-P),mefenpyr (-diethyl), MG-191, oxabetrinil, PPG-1292, R-29148.

A mixture with other known active compounds, such as fungicides,insecticides, acaricides, nematicides, bird repellents, plant nutrientsand agents which improve soil structure, is also possible.

The active compounds can be used as such, in the form of theirformulations or in the use forms prepared therefrom by further dilution,such as ready-to-use solutions, suspensions, emulsions, powders, pastesand granules. They are used in a customary manner, for example bywatering, spraying, atomizing or broadcasting.

The active compounds according to the invention can be applied bothbefore and after emergence of the plants. They can also be incorporatedinto the soil before sowing.

The amount of active compound used can vary within a relatively widerange. It depends essentially on the nature of the desired effect. Ingeneral, the amounts used are between 1 g and 10 kg of active compoundper hectare of soil surface, preferably between 5 g and 5 kg per ha.

The substances according to the invention have potent microbicidalactivity and can be employed for controlling unwanted microorganisms,such as fungi and bacteria, in crop protection and in the protection ofmaterials.

Fungicides can be employed in crop protection for controllingPlasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes,Ascomycetes, Basidiomycetes and Deuteromycetes.

Bactericides can be employed in crop protection for controllingPseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceaeand Streptomycetaceae.

Some pathogens causing fungal and bacterial diseases which come underthe generic names listed above may be mentioned as examples, but not byway of limitation:

Xanthomonas species, such as, for example, Xanthomonas campestris pv.oryzae;

Pseudomonas species, such as, for example, Pseudomonas syringae pv.lachrymans;

Erwinia species, such as, for example, Erwinia amylovora;

Pythium species, such as, for example, Pythium ultimum;

Phytophthora species, such as, for example, Phytophthora infestans;

Pseudoperonospora species, such as, for example, Pseudoperonosporahumuli or Pseudoperonospora cubensis;

Plasmopara species, such as, for example, Plasmopara viticola;

Bremia species, such as, for example, Bremia lactucae;

Peronospora species, such as, for example, Peronospora pisi or P.brassicae;

Erysiphe species, such as, for example, Erysiphe graminis;

Sphaerotheca species, such as, for example, Sphaerotheca fuliginea;

Podosphaera species, such as, for example, Podosphaera leucotricha;

Venturia species, such as, for example, Venturia inaequalis;

Pyrenophora species, such as, for example, Pyrenophora teres or P.graminea (conidia form: Drechslera, syn: Helminthosporium);

Cochliobolus species, such as, for example, Cochliobolus sativus(conidia form: Drechslera, syn: Helminthosporium);

Uromyces species, such as, for example, Uromyces appendiculatus;

Puccinia species, such as, for example, Puccinia recondita;

Sclerotinia species, such as, for example, Sclerotinia sclerotiorum;

Tilletia species, such as, for example, Tilletia caries;

Ustilago species, such as, for example, Ustilago nuda or Ustilagoavenae;

Pellicularia species, such as, for example, Pellicularia sasakii;

Pyricularia species, such as, for example, Pyricularia oryzae;

Fusarium species, such as, for example, Fusarium culmorum;

Botrytis species, such as, for example, Botrytis cinerea;

Septoria species, such as, for example, Septoria nodorum;

Leptosphaeria species, such as, for example, Leptosphaeria nodorum;

Cercospora species, such as, for example, Cercospora canescens;

Alternaria species, such as, for example, Alternaria brassicae; and

Pseudocercosporella species, such as, for example, Pseudocercosporellaherpotrichoides.

The active compounds according to the invention also have very goodfortifying action in plants. Accordingly, they can be used formobilizing the defences of the plant against attack by unwantedmicroorganisms.

In the present context, plant-fortifying (resistance-inducing)substances are to be understood as meaning those substances which arecapable of stimulating the defence system of plants such that, when thetreated plants are subsequently inoculated with unwanted microorganisms,they show substantial resistance against these mircroorganisms.

In the present case, undesirable microorganisms are to be understood asmeaning phytopathogenic fungi, bacteria and viruses. Accordingly, thesubstances according to the invention can be used to protect plants fora certain period after the treatment against attack by the pathogensmentioned. The period for which protection is provided generally extendsover 1 to 10 days, preferably 1 to 7 days, after the treatment of theplants with the active compounds.

The fact that the active compounds are well tolerated by plants at theconcentrations required for controlling plant diseases permits thetreatment of above-ground parts of plants, of propagation stock andseeds, and of the soil.

The active compounds according to the invention are also suitable forincreasing the yield of crops. In addition, they show reduced toxicityand are well tolerated by plants.

At certain concentrations and application rates, the active compoundsaccording to the invention can also be used as herbicides, forinfluencing plant growth and for controlling animal pests. Ifappropriate, they can also be used as intermediates and precursors forthe synthesis of further active compounds.

In the protection of materials, the compounds according to the inventioncan be employed for protecting industrial materials against infectionwith, and destruction by, undesired microorganisms.

Industrial materials in the present context are understood as meaningnon-living materials which have been prepared for use in industry. Forexample, industrial materials which are intended to be protected byactive compounds according to the invention from microbial change ordestruction can be adhesives, sizes, paper and board, textiles, leather,wood, paints and plastic articles, cooling lubricants and othermaterials which can be infected with, or destroyed by, microorganisms.Parts of production plants, for example cooling-water circuits, whichmay be impaired by the proliferation of microorganisms may also bementioned within the scope of the materials to be protected. Industrialmaterials which may be mentioned within the scope of the presentinvention are preferably adhesives, sizes, paper and board, leather,wood, paints, cooling lubricants and heat-transfer liquids, particularlypreferably wood.

Microorganisms capable of degrading or changing the industrial materialswhich may be mentioned are, for example, bacteria, fungi, yeasts, algaeand slime organisms. The active compounds according to the inventionpreferably act against fungi, in particular moulds, wood-discolouringand wood-destroying fungi (Basidiomycetes), and against slime organismsand algae.

Microorganisms of the following genera may be mentioned as examples:

Alternaria, such as Alternaria tenuis,

Aspergillus, such as Aspergillus niger,

Chaetomium, such as Chaetomium globosum,

Coniophora, such as Coniophora puetana,

Lentinus, such as Lentinus tigrinus,

Penicillium, such as Penicillium glaucum,

Polyporus, such as Polyporus versicolor,

Aureobasidium, such as Aureobasidium pullulans,

Sclerophoma, such as Sclerophoma pityophila,

Trichoderma, such as Trichoderma viride,

Escherichia, such as Escherichia coli,

Pseudomonas, such as Pseudomonas aeruginosa, and

Staphylococcus, such as Staphylococcus aureus.

Depending on their particular physical and/or chemical properties, theactive compounds can be converted into the customary formulations, suchas solutions, emulsions, suspensions, powders, foams, pastes, granules,aerosols and microencapsulations in polymeric substances and in coatingcompositions for seeds, and ULV cool and warm fogging formulations.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is, liquid solvents, liquefiedgases under pressure, and/or solid carriers, optionally with the use ofsurfactants, that is emulsifiers and/or dispersants, and/or foamformers. If the extender used is water, it is also possible to employ,for example, organic solvents as auxiliary solvents. Essentially,suitable liquid solvents are: aromatics such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics or chlorinated aliphatichydrocarbons such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons such as cyclohexane or paraffins, forexample petroleum fractions, alcohols such as butanol or glycol andtheir ethers and esters, ketones such as acetone, methyl ethyl ketone,methyl isobutyl ketone or cyclohexanone, strongly polar solvents such asdimethylformamide and dimethyl sulphoxide, or else water. Liquefiedgaseous extenders or carriers are to be understood as meaning liquidswhich are gaseous at standard temperature and under atmosphericpressure, for example aerosol propellants such as halogenatedhydrocarbons, or else butane, propane, nitrogen and carbon dioxide.Suitable solid carriers are: for example ground natural minerals such askaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite ordiatomaceous earth, and ground synthetic minerals such as finely dividedsilica, alumina and silicates. Suitable solid carriers for granules are:for example crushed and fractionated natural rocks such as calcite,marble, pumice, sepiolite and dolomite, or else synthetic granules ofinorganic and organic meals, and granules of organic material such assawdust, coconut shells, maize cobs and tobacco stalks. Suitableemulsifiers and/or foam formers are: for example nonionic and anionicemulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylenefatty alcohol ethers, for example alkylaryl polyglycol ethers,alkylsulphonates, alkyl sulphates, arylsulphonates, or else proteinhydrolysates. Suitable dispersants are: for example lignosulphite wasteliquors and methylcellulose.

Tackifiers such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, or else naturalphospholipids such as cephalins and lecithins and syntheticphospholipids can be used in the formulations. Other possible additivesare mineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs suchas alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs,and trace nutrients such as salts of iron, manganese, boron, copper,cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95% by weight ofactive compound, preferably between 0.5 and 90%.

The active compounds according to the invention can be used as such orin their formulations, also in a mixture with known fungicides,bactericides, acaricides, nematicides or insecticides, to broaden, forexample, the activity spectrum or to prevent development of resistance.In many cases, synergistic effects are obtained, i.e. the activity ofthe mixture is greater than the activity of the individual components.

Examples of suitable mixing components are the following:

Fungicides:

2-phenylphenol; 8-hydroxyquinoline sulphate; acibenzolar-S-methyl;aldimorph; amidoflumet; ampropylfos; ampropylfos-potassium; andoprim;anilazine; azaconazole; azoxystrobin; benalaxyl; benodanil; benomyl;benthiavalicarb-isopropyl; benzamacril; benzamacril-isobutyl; bilanafos;binapacryl; biphenyl; bitertanol; blasticidin-S; bromuconazole;bupirimate; buthiobate; butylamine; calcium polysulphide; capsimycin;captafol; captan; carbendazim; carboxin; carpropamid; carvone;chinomethionat; chlobenthiazone; chlorfenazole; chloroneb;chlorothalonil; chlozolinate; clozylacon; cyazofamid; cyflufenamid;cymoxanil; cyproconazole; cyprodinil; cyprofuram; Dagger G; debacarb;dichlofluanid; dichlone; dichlorophen; diclocymet; diclomezine;dicloran; diethofencarb; difenoconazole; diflumetorim; dimethirimol;dimethomorph; dimoxystrobin; diniconazole; diniconazole-M; dinocap;diphenylamine; dipyrithione; ditalimfos; dithianon; dodine; drazoxolon;edifenphos; epoxiconazole; ethaboxam; ethirimol; etridiazole;famoxadone; fenamidone; fenapanil; fenarimol; fenbuconazole; fenfuram;fenhexamid; fenitropan; fenoxanil; fenpiclonil; fenpropidin;fenpropimorph; ferbam; fluazinam; flubenzimine; fludioxonil; flumetover;flumorph; fluoromide; fluoxastrobin; fluquinconazole; flurprimidol;flusilazole; flusulfamide; flutolanil; flutriafol; folpet; fosetyl-Al;fosetyl-sodium; fuberidazole; furalaxyl; furametpyr; furcarbanil;furmecyclox; guazatine; hexachlorobenzene; hexaconazole; hymexazole;imazalil; imibenconazole; iminoctadine triacetate; iminoctadinetris(albesil); iodocarb; ipconazole; iprobenfos; iprodione;iprovalicarb; irumamycin; isoprothiolane; isovaledione; kasugamycin;kresoxim-methyl; mancozeb; maneb; meferimzone; mepanipyrim; mepronil;metalaxyl; metalaxyl-M; metconazole; methasulfocarb; methfuroxam;metiram; metominostrobin; metsulfovax; mildiomycin; myclobutanil;myclozolin; natamycin; nicobifen; nitrothal-isopropyl; noviflumuron;nuarimol; ofurace; orysastrobin; oxadixyl; oxolinic acid; oxpoconazole;oxycarboxin; oxyfenthiin; paclobutrazole; pefurazoate; penconazole;pencycuron; phosdiphen; phthalide; picoxystrobin; piperalin; polyoxins;polyoxorim; probenazole; prochloraz; procymidone; propamocarb;propanosine-sodium; propiconazole; propineb; proquinazid;prothioconazole; pyraclostrobin; pyrazophos; pyrifenox; pyrimethanil;pyroquilon; pyroxyfur; pyrrolenitrine; quinconazole; quinoxyfen;quintozene; simeconazole; spiroxamine; sulphur; tebuconazole;tecloftalam; tecnazene; tetcyclacis; tetraconazole; thiabendazole;thicyofen; thifluzamide; thiophanate-methyl; thiram; tioxymid;tolclofos-methyl; tolylfluanid; triadimefon; triadimenol; triazbutil;triazoxide; tricyclamide; tricyclazole; tridemorph; trifloxystrobin;triflumizole; triforine; triticonazole; uniconazole; validamycin A;vinclozolin; zineb; ziram; zoxamide;(2S)-N-[2-[4-[[3-(4-chlorophenyl)-2-propynyl]oxy]-3-methoxyphenyl]ethyl]-3-methyl-2-[(methylsulphonyl)amino]butanamide;1-(1-naphthalenyl)-1H-pyrrole-2,5-dione;2,3,5,6-tetrachloro-4-(methylsulphonyl)pyridine;2-amino-4-methyl-N-phenyl-5-thiazolecarboxamide;2-chloro-N-(2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl)-3-pyridinecarboxamide;3,4,5-trichloro-2,6-pyridinedicarbonitrile; actinovate;cis-1-[4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)cycloheptanol; methyl1-(2,3-dihydro-2,2-dimethyl-1H-inden-1-yl)-1H-imidazole-5-carboxylate;monopotassium carbonate;N-(6-methoxy-3-pyridinyl)-cyclopropanecarboxamide;N-butyl-8-(1,1-dimethylethyl)-1-oxaspiro[4.5]decane-3-amine; sodiumtetrathiocarbonate;

and copper salts and preparations, such as Bordeaux mixture; copperhydroxide; copper naphthenate; copper oxychloride; copper sulphate;cufraneb; copper oxide; mancopper; oxine-copper.

Bactericides:

bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate,kasugamycin, octhilinone, furancarboxylic acid, oxytetracyclin,probenazole, streptomycin, teclof-talam, copper sulphate and othercopper preparations.

Insecticides/Acaricides/Nematicides:

abamectin, ABG-9008, acephate, acequinocyl, acetamiprid, acetoprole,acrinathrin, AKD-1022, AKD-3059, AKD-3088, alanycarb, aldicarb,aldoxycarb, allethrin, allethrin 1R-isomers, alpha-cypermethrin(alphamethrin), amidoflumet, aminocarb, amitraz, avermectin, AZ-60541,azadirachtin, azamethiphos, azinphos-methyl, azin-phos-ethyl,azocyclotin,

Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis, Bacillusthuringiensis, Bacillus thuringiensis strain EG-2348, Bacillusthuringiensis strain GC-91, Bacillus thuringiensis strain NCTC-11821,baculoviruses, Beauveria bassiana, Beauveria tenella, bendiocarb,benfuracarb, bensultap, benzoximate, beta-cyfluthrin,beta-cyper-methrin, bifenazate, bifenthrin, binapacryl, bioallethrin,bioallethrin-S-cyclopentyl-isomer, bioethanomethrin, biopermethrin,bioresmethrin, bistrifluron, BPMC, brofen-prox, bromophos-ethyl,bromopropylate, bromfenvinfos (-methyl), BTG-504, BTG-505, bufencarb,buprofezin, butathiofos, butocarboxim, butoxycarboxim, butyl-pyridaben,

cadusafos, camphechlor, carbaryl, carbofuran, carbophenothion,carbosulfan, cartap, CGA-50439, chinomethionat, chlordane,chlordimeform, chloethocarb, chlorethoxyfos, chlorfenapyr,chlorfenvinphos, chlorfluazuron, chlormephos, chlorobenzilate,chloropicrin, chlorproxyfen, chlorpyrifos-methyl, chlorpyrifos (-ethyl),chlovapothrin, chromafenozide, cis-cypermethrin, cis-resmethrin,cis-permethrin, clocythrin, cloethocarb, clofentezine, clothianidin,clothiazoben, codlemone, coumaphos, cyanofenphos, cyanophos, cycloprene,cycloprothrin, Cydia pomonella, cyfluthrin, cyhalothrin, cyhexatin,cypermethrin, cyphenothrin (1R-trans-isomer), cyromazine,

DDT, deltamethrin, demeton-S-methyl, demeton-S-methylsulphone,diafenthiuron, dialifos, diazinon, dichlofenthion, dichlorvos, dicofol,dicrotophos, dicyclanil, diflubenzuron, dimethoate, dimethylvinphos,dinobuton, dinocap, dinotefuran, diofenolan, disulfoton, docusat-sodium,dofenapyn, DOWCO-439,

eflusilanate, emamectin, emamectin-benzoate, empenthrin (1R-isomer),endosulfan, Entomopthora spp., EPN, esfenvalerate, ethiofencarb,ethiprole, ethion, ethoprophos, etofenprox, etoxazole, etrimfos,

famphur, fenamiphos, fenazaquin, fenbutatin oxide, fenfluthrin,fenitrothion, fenobucarb, fenothiocarb, fenoxacrim, fenoxycarb,fenpropathrin, fenpyrad, fenpyrithrin, fenpyroximate, fensulfothion,fenthion, fentrifanil, fenvalerate, fipronil, flonicamid, fluacrypyrim,fluazuron, flubenzimine, flubrocythrinate, flucycloxuron, flucythrinate,flufenerim, flufenoxuron, flufenprox, flumethrin, flupyrazofos,flutenzin (flufenzine), fluvalinate, fonofos, formetanate, formothion,fosmethilan, fosthiazate, fubfenprox (fluproxyfen), furathiocarb,

gamma-HCH, gossyplure, grandlure, granulosis viruses, halofenprox,halofenozide, HCH, HCN-801, heptenophos, hexaflumuron, hexythiazox,hydramethylnone, hydroprene,

IKA-2002, imidacloprid, imiprothrin, indoxacarb, iodofenphos,iprobenfos, isazofos, isofenphos, isoprocarb, isoxathion, ivermectin,

japonilure,

kadethrin, nuclear polyhedrosis viruses, kinoprene,

lambda-cyhalothrin, lindane, lufenuron,

malathion, mecarbam, mesulfenfos, metaldehyde, metam-sodium,methacrifos, methamidophos, Metharhizium anisopliae, Metharhiziumflavoviride, methidathion, methiocarb, methomyl, methoprene,methoxychlor, methoxyfenozide, metolcarb, metoxadiazone, mevinphos,milbemectin, milbemycin, MKI-245, MON-45700, monocrotophos, moxidectin,MTI-800,

naled, NC-104, NC-170, NC-184, NC-194, NC-196, niclosamide, nicotine,nitenpyram, nithiazine, NNI-0001, NNI-0101, NNI-0250, NNI-9768,novaluron, noviflumuron,

OK-5101, OK-5201, OK-9601, OK-9602, OK-9701, OK-9802, omethoate, oxamyl,oxydemeton-methyl,

Paecilomyces fumosoroseus, parathion-methyl, parathion (-ethyl),permethrin (cis-, trans-), petroleum, PH-6045, phenothrin (1R-transisomer), phenthoate, phorate, phosalone, phosmet, phosphamidon,phosphocarb, phoxim, piperonyl butoxide, pirimicarb, pirimiphos-methyl,pirimiphos-ethyl, prallethrin, profenofos, promecarb, propaphos,propargite, propetamphos, propoxur, prothiofos, prothoate,protrifenbute, pymetrozine, pyraclofos, pyresmethrin, pyrethrum,pyridaben, pyridalyl, pyridaphenthion, pyridathion, pyrimidifen,pyriproxyfen,

quinalphos,

resmethrin, RH-5849, ribavirin, RU-12457, RU-15525,

S-421, S-1833, salithion, sebufos, SI-0009, silafluofen, spinosad,spirodiclofen, spiromesifen, sulfluramid, sulfotep, sulprofos, SZI-121,

tau-fluvalinate, tebufenozide, tebufenpyrad, tebupirimfos,teflubenzuron, tefluthrin, temephos, temivinphos, terbam, terbufos,tetrachlorvinphos, tetradifon, tetramethrin, tetramethrin (1R-isomer),tetrasul, theta-cypermethrin, thiacloprid, thiamethoxam, thiapronil,thiatriphos, thiocyclam hydrogenoxalate, thiodicarb, thiofanox,thiometon, thiosultap-sodium, thuringiensin, tolfenpyrad, tralocythrin,tralomethrin, transfluthrin, triarathene, triazamate, triazophos,triazuron, trichlophenidine, trichlorfon, triflumuron, trimethacarb,

vamidothion, vaniliprole, verbutin, Verticillium lecanii,

WL-108477, WL-40027,

YI-5201, YI-5301, YI-5302,

XMC, xylylcarb,

ZA-3274, zeta-cypermethrin, zolaprofos, ZXI-8901,

the compound 3-methylphenyl propylcarbamate (tsumacide Z),

the compound3-(5-chloro-3-pyridinyl)-8-(2,2,2-trifluoroethyl)-8-azabicyclo[3.2.1]-octane-3-carbonitrile(CAS-Reg. No. 185982-80-3) and the corresponding 3-endo-isomer (CAS-Reg.No. 185984-60-5) (cf. WO-96/37494, WO-98/25923),

and preparations which comprise insecticidally active plant extracts,nematodes, fungi or viruses.

A mixture with other known active compounds, such as herbicides, or withfertilizers and growth regulators, is also possible.

In addition, the compounds of the formula (I) according to the inventionalso have very good antimycotic activity. They have a very broadantimycotic activity spectrum in particular against dermatophytes andyeasts, moulds and diphasic fungi (for example against Candida species,such as Candida albicans, Candida glabrata), and Epidermophytonfloccosum, Aspergillus species, such as Aspergillus niger andAspergillus fumigatus, Trichophyton species, such as Trichophytonmentagrophytes, Microsporon species such as Microsporon canis andaudouinii. The list of these fungi by no means limits the mycoticspectrum covered, but is only for illustration.

The active compounds can be used as such, in the form of theirformulations or the use forms prepared therefrom, such as ready-to-usesolutions, suspensions, wettable powders, pastes, soluble powders, dustsand granules. Application is carried out in a customary manner, forexample by watering, spraying, atomizing, broadcasting, dusting,foaming, spreading, etc. It is furthermore possible to apply the activecompounds by the ultra-low-volume method, or to inject the activecompound preparation or the active compound itself into the soil. It isalso possible to treat the seeds of the plants.

When using the active compounds according to the invention asfungicides, the application rates can be varied within a relatively widerange, depending on the kind of application. For the treatment of partsof plants, the active compound application rates are generally between0.1 and 10,000 g/ha, preferably between 10 and 1000 g/ha. For seeddressing, the active compound application rates are generally between0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 gper kilogram of seed. For the treatment of the soil, the active compoundapplication rates are generally between 0.1 and 10,000 g/ha, preferablybetween 1 and 5000 g/ha.

The preparation and the use of the active compounds according to theinvention is illustrated by the examples below.

PREPARATION EXAMPLES Example No. I-1-1

At 0-5° C., 0.24 ml of sulphuryl chloride and 1 ml of absolutechloroform are added dropwise to 0.98 g of the compound of ExampleI-1-a-18 (WO 99/48869) in 30 ml of absolute chloroform. After 30 min,the reaction has ended (monitored by thin-layer chromatography).

The reaction mixture is washed with NaHCO₃ solution, the organic phaseis dried and the solvent is distilled off.

Yield: 0.85 g (78% of theory), m.p. 175° C.

Example No. I-1-29

At room temperature, 0.33 g (5.2 mmol) of fuming nitric acid is addeddropwise to 0.98 g of the compound of Example I-1-a-18 (WO 99/48869) in45 ml of absolute chloroform. After 30 min, the reaction has ended(monitored by thin-layer chromatography).

The reaction mixture is added to 40 ml of ice-water, the organic phaseis separated off, the aqueous phase is extracted with dichloromethaneand the combined organic phases are dried. The solvent is then distilledoff. The residue is purified by silica gel column chromatography(dichloromethane, ethyl acetate, 10:1).

Yield: 0.75 g (67% of theory), m.p. 157° C.

Analogously to Example (I-1-1) and in accordance with the generalstatements for the preparation, the following compounds of the formula(I-1) were obtained

TABLE A Ex. No. W X Y Z D G A B m.p. ° C. I-1-2 H Cl 5-(4-Cl—C₆H₄) H HCl CH₃ CH₃ 173 I-1-3 H CH₃ 5-(3-Cl—C₆H₄) H H Cl CH₃ CH₃ 188 I-1-4 CH₃CH₃ 4-(3-Cl—C₆H₄) H H Cl (CH₂)₂—CHOCH₃(CH₂)₂— 165 I-1-5 CH₃ CH₃4-(4-CH₃—C₆H₄) H H Cl (CH₂)₂—CHOCH₃(CH₂)₂— 281 I-1-6 H CH₃ 5-(4-Cl—C₆H₄)4-CH₃ H Cl —(CH₂)₂—O—(CH₂)₂— 208 I-1-7 H CH₃ 5-(4-Cl—C₆H₄) 4-CH₃ H Cl—CH₂—O—(CH₂)₃— 204 I-1-8 Cl CH₃ 4-(4-Cl—C₆H₄) H H Cl —CH₂—O—(CH₂)₃— 324I-1-9 Cl CH₃ 4-(4-Cl—C₆H₄) H H Cl —(CH₂)₂—CHOC₂H₅—(CH₂)₂— 291 I-1-10 CH₃C₂H₅ 4-(4-Cl—C₆H₄) H H Cl —(CH₂)₂—CHOC₂H₅—(CH₂)₂— 258 I-1-11 H CH₃5-(4-Cl—C₆H₄) H H Cl i-C₃H₇ CH₃ 192 I-1-12 H Cl 5-(3-Cl—C₆H₄) H H Cl—(CH₂)₂—CHOCH₃—(CH₂)₂— 228 I-1-13 H CH₃ 5-(3,4-Cl₂—C₆H₃) H H Cl—(CH₂)₂—CHOCH₃—(CH₂)₂— 203 I-1-14 H CH₃ 5-(4-Cl—C₆H₄) H H Cl—(CH₂)₂—O—(CH₂)₂— 218 I-1-15 H CH₃ 5-(3,4-Cl₂—C₆H₃) H H Cl CH₃ CH₃ 222I-1-16 H Cl 5-(4-Cl—C₆H₄) H H Cl —(CH₂)₂—O—(CH₂)₂— 250 I-1-17 H Cl5-(4-Cl—C₆H₄) H H Cl —(CH₂)₂—CHi-C₃H₇—(CH₂)₂— 276 I-1-18 H CH₃5-(4-Cl—C₆H₄) H H Cl —(CH₂)₂—CHn-C₃H₇—(CH₂)₂— 223 I-1-19 H CH₃5-(4-Cl—C₆H₄) H H Cl —(CH₂)₂—CHi-C₃H₇—(CH₂)₂ 245 I-1-20 H Cl5-(4-Cl—C₆H₄) H H Cl —(CH₂)₄— 227 I-1-21 H CH₃ 5-(4-Cl—C₆H₄) H H Cl—(CH₂)₂— 219 I-1-22 H CH₃ 5-(4-Cl—C₆H₄) H H Cl —CH₂—CHCH₃—(CH₂)₃— 227I-1-23 H Cl 5-(4-Cl—C₆H₄) H H Cl —CH₂—CHCH₃—(CH₂)₃— 286 I-1-24 H Cl5-(4-Cl—C₆H₄) H H Cl —(CH₂)₅— 269 I-1-25 H Cl 5-(4-Cl—C₆H₄) H H Cl—(CH₂)₂—CHn-C₃H₇—(CH₂)₂— 255 I-1-26 H CH₃ 5-(4-Cl—C₆H₄) H H Cl —(CH₂)₅—228 I-1-27 H Cl 5-(4-Cl—C₆H₄) H H Cl —(CH₂)₂—CHCH₃—(CH₂)₂— 290 I-1-28 HCH₃ 5-(4-Cl—C₆H₄) H H Cl —(CH₂)— 289 I-1-29 H CH₃ 5-(4-Cl—C₆H₄) H H NO₂CH₃ CH₃ 157

Example I-2-1

With ice-cooling, a solution of sulphuryl chloride (0.164 g) in 10 ml ofabsolute chloroform is added dropwise to a solution of 0.4 g of3-[2-methyl-5-(4-chloro-phenyl)phenyl]-5,5-dimethyl-4-hydroxy-Δ³-furan-2-onein 10 ml of absolute chloroform, and the mixture is then stirred withice-cooling for 30 min.

The reaction mixture is then washed with water, saturated sodiumbicarbonate solution and saturated sodium chloride solution and dried.

Yield: 0.4 g (72% of theory), log P (pH 2.5) 4.8.

Analogously to Example (I-2-1) and in accordance with the generalstatements about the preparation, the compounds of the formula (I-2)were obtained

TABLE B Ex. No. W X Y Z G A B m.p. ° C. I-2-2 H CH₃ 5-(4-Cl—C₆H₄) H Cl—(CH₂)₂—CHOCH₃—(CH₂)₂ 144-146 I-2-3 H CH₃ 5-(4-Cl—C₆H₄) H Cl —(CH₂)₅—150 I-2-4 H CH₃ 5-(3-Cl—C₆H₄) H Cl —(CH₂)₂—CHCF₃—(CH₂)₂— 108-110 I-2-5 HCH₃ 5-(4-Cl—C₆H₄) H Cl i-C₃H₇ CH₃ logP 5.61 I-2-6 H CH₃ 5-(4-Cl—C₆H₄)4-CH₃ Cl —(CH₂)₄— logP 5.56 I-2-7 H C₂H₅ 5-(4-Cl—C₆H₄) H Cl CH₃ CH₃ logP5.05 I-2-8 H CH₃ 5-(4-CN—C₆H₄) H Cl CH₃ CH₃ 198 I-2-9 H CH₃5-(4-CN—C₆H₄) H Cl —(CH₂)₄— 196 I-2-10 H CH₃ 5-(4-F—C₆H₄) H Cl CH₃ CH₃133-135 I-2-11 H CH₃ 5-(3-F—C₆H₄) H Cl CH₃ CH₃ log P 4.30 I-2-12 CH₃ CH₃4-(4-Cl—C₆H₄) H Cl —(CH₂)₅— 262 I-2-13 CH₃ C₂H₅ 4-(4-Cl—C₆H₄) H Cl—(CH₂)₂—CHOC₂H₅—(CH₂)₂— log P 5.59 I-2-14 CH₃ CH₃ 4-(4-Cl—C₆H₄) H Cl CH₃CH₃ log P 5.11 I-2-15 CH₃ CH₃ 4-(4-Cl—C₆H₄) H Cl —(CH₂)₄— 152-155 I-2-16CH₃ CH₃ 4-(4-Cl—C₆H₄) H Cl —(CH₂)₂—CHCH₃—(CH₂)₂— 85-88 I-2-17 CH₃ CH₃4-(4-Cl—C₆H₄) H Cl —CH₂—O—(CH₂)₃— log P 4.91 I-2-18 CH₃ CH₃4-(4-Cl—C₆H₄) H Cl —(CH₂)₂—O—(CH₂)₂— 178-180 logP determined at pH = 2.3

The stated log P values were determined in accordance with EEC Directive79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) usinga reversed-phase column (C 18). Temperature: 43° C.

-   -   (a) Mobile phases for the determination in the acidic range:        0.1% aqueous phosphoric acid, acetonitrile; linear gradient from        10% acetonitrile to 90% acetonitrile.    -   (b) Mobile phases for the determination in the neutral range:        0.01 molar aqueous phosphate buffer solution, acetonitrile;        linear gradient from 10% acetonitrile to 90% acetonitrile.

Calibration was carried out using unbranched alkan-2-ones (of 3 to 16carbon atoms) with known log P values (determination of the log P valuesby the retention times using linear interpolation between two successivealkanones).

The lambda max values were determined in the maxima of thechromatographic signals using the UV spectra from 200 nm to 400 nm.

Example I-3-1

With ice-cooling, 0.10 ml of sulphuryl chloride in 0.5 ml of absolutechloroform is added dropwise to 0.385 g of Example I-3-a-1 (WO 99/48869)in 10 ml of absolute chloroform. The mixture is stirred for 20 min.

The reaction mixture is washed with NaHCO₃ solution, the organic phaseis dried and the solvent is distilled off. For further purification, theproduct is repeatedly triturated with cyclohexane/ethyl acetate.

Yield: 0.315 g (75% of theory), m.p. 157-160° C.

TABLE C Analogously to Example (I-3-1) and in accordance with thegeneral statements about the preparation, the following compounds of theformula (I-3) were obtained: (I-3)

Ex. m.p. No. W X Y Z G A B ° C. I-3-2 H CH₃ 5-(4-Cl—C₆H₄) 4- Cl —(CH₂)₅—wax CH₃

Example A Myzus Test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 2 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with emulsifier-containingwater to the desired concentration.

Cabbage leaves (Brassica oleracea) which are heavily infested by thegreen peach aphid (Myzus persicae) are treated by being dipped into thepreparation of active compound of the desired concentration.

After the desired period of time, the kill in % is determined. 100%means that all aphids have been killed; 0% means that none of the aphidshave been killed.

In this test, for example, the following compounds of the PreparationExamples show good activity:

TABLE A Plant-damaging insects Myzus persicae test Concentration ofactive Active compound compound in ppm Kill rate in % after 6^(d) Ex.I-1-1 500 95 Ex. I-1-14 500 100 Ex. I-1-6 500 98 Ex. I-1-7 500 100 Ex.I-1-9 500 95 Ex. I-1-13 500 100 Ex. I-1-15 500 95

Example B Phaedon Larvae Test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 2 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with emulsifier-containingwater to the desired concentration.

Cabbage leaves (Brassica oleracea) are treated by being dipped into thepreparation of active compound of the desired concentration and arepopulated with larvae of the mustard beetle (Phaedon cochleariae) whilethe leaves are still moist.

After the desired period of time, the kill in % is determined. 100%means that all beetle larvae have been killed; 0% means that none of thebeetle larvae have been killed.

In this test, for example, the following compounds of the PreparationExamples show good activity:

TABLE B Plant-damaging insects Phaedon larvae test Concentration ofactive Active compound compound in ppm Kill rate in % after 7^(d) Ex.I-2-1 1000 100 Ex. I-1-2 500 100 Ex. I-1-1 500 100 Ex. I-1-3 500 100 Ex.I-1-14 500 100 Ex. I-1-6 500 100 Ex. I-1-7 500 100 Ex. I-1-9 500 100 Ex.I-1-11 500 100 Ex. I-1-12 500 100 Ex. I-1-13 500 100 Ex. I-1-15 500 100Ex. I-3-1 500 100

Example C Plutella Test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 2 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with emulsifier-containingwater to the desired concentration.

Cabbage leaves (Brassica oleracea) are treated by being dipped into thepreparation of active compound of the desired concentration and arepopulated with caterpillars of the diamondback moths (Plutellaxylostella) while the leaves are still moist.

After the desired period of time, the kill in % is determined. 100%means that all caterpillars have been killed; 0% means that none of thecaterpillars have been killed.

In this test, for example, the following compounds of the PreparationExamples show good activity:

TABLE C Plant-damaging insects Plutella test Concentration of activeActive compound compound in ppm Kill rate in % after 7^(d) Ex. I-1-11500 100 Ex. I-1-12 500 100 Ex. I-1-13 500 100 Ex. I-1-15 500 100

Example D Spodoptera exigua Test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 2 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with emulsifier-containingwater to the desired concentration.

Cabbage leaves (Brassica oleracea) are treated by being dipped into thepreparation of active compound of the desired concentration and arepopulated with caterpillars of the armyworm (Spodoptera exigua) whilethe leaves are still moist.

After the desired period of time, the kill in % is determined. 100%means that all caterpillars have been killed; 0% means that none of thecaterpillars have been killed.

In this test, for example, the following compounds of the PreparationExamples show good activity:

TABLE D Plant-damaging insects Spodoptera exigua test Concentration ofactive Active compound compound in ppm Kill rate in % after 7^(d) Ex.I-1-11 500 90 Ex. I-1-13 500 100 Ex. I-1-15 500 100

Example E Spodoptera frugiperda Test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 2 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with emulsifier-containingwater to the desired concentration.

Cabbage leaves (Brassica oleracea) are treated by being dipped into thepreparation of active compound of the desired concentration and arepopulated with caterpillars of the armyworm (Spodoptera frugiperda)while the leaves are still moist.

After the desired period of time, the kill in % is determined. 100%means that all caterpillars have been killed; 0% means that none of thecaterpillars have been killed.

In this test, for example, the following compounds of the PreparationExamples show good activity:

TABLE E Plant-damaging insects Spodoptera frugiperda test Concentrationof active Active compound compound in ppm Kill rate in % after 7^(d) Ex.I-2-1 1000 100 Ex. I-1-2 500 100 Ex. I-1-1 500 100 Ex. I-1-14 500 100Ex. I-1-6 500 100 Ex. I-1-7 500 100 Ex. I-1-11 500 100 Ex. I-1-12 500100 Ex. I-1-13 500 100 Ex. I-1-15 500 100

Example F Tetranychus Test OP-Resistent/Dip Treatment

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 2 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with emulsifier-containingwater to the desired concentration.

Bean plants (Phaseolus vulgaris) which are heavily infested by allstages of the greenhouse red spider mite (Tetranychus urticae) aredipped into a preparation of active compound of the desiredconcentration.

After the desired period of time, the effect in % is determined. 100%means that all spider mites have been killed; 0% means that none of thespider mites have been killed.

In this test, for example, the following compounds of the PreparationExamples show good activity:

TABLE F Plant-damaging mites Tetranychus test (OP-resistent/diptreatment) Concentration of active Active compound compound in ppm Killrate in % after 7^(d) Ex. I-2-1 100 98 Ex. I-1-2 100 100 Ex. I-1-1 100100 Ex. I-1-14 100 99 Ex. I-1-6 100 99 Ex. I-1-7 100 98 Ex. I-1-8 100 98Ex. I-1-11 100 99 Ex. I-1-12 100 100 Ex. I-1-13 100 95 Ex. I-1-15 100 99

Example G In Vitro Test for the ED₅₀ Determination in Microorganisms

A methanolic solution of the active compound to be tested, admixed withemulsifier PS16, is pipetted into the wells of microtiter plates. Afterthe solvent has evaporated, 200 μl of potato/dextrose medium are addedto each well.

Beforehand, a suitable concentration of spores or mycelium of the fungusto be tested was added to the medium.

The resulting concentrations of the active compound are 0.1, 1, 10 and100 ppm. The resulting concentration of the emulsifier is 300 ppm.

The plates are then incubated on a shaker at a temperature of 22° C. for3-5 days, until sufficient growth can be observed in the untreatedcontrol.

Evaluation is carried out photometrically at a wavelength of 620 nm. Thedose of active compound which causes 50% inhibition of fungal growthcompared to the untreated control (ED₅₀) is calculated from the datameasured at different concentrations.

TABLE G In vitro test for the ED₅₀ determination in microorganismsActive compound Microorganism ED₅₀ Ex. I-3-1 Botrytis cinerea <0.10Pyricularia oryzae <0.10 Septoria tritici 0.61 Ustilago avenae 0.27

Example H Post-Emergence Test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, thestated amount of emulsifier is added and the concentrate is diluted withwater to the desired concentration.

Test plants of a height of 5-15 cm are sprayed with the preparation ofactive compound such that the particular amounts of active compounddesired are applied per unit area. The concentration of the spray liquoris chosen such that the particular amounts of active compound desiredare applied in 1000 l of water/ha.

After three weeks, the degree of damage to the plants is rated in %damage in comparison to the development of the untreated control.

The figures denote:

-   -   0%=no effect (like untreated control)    -   100%=total destruction

Example I Pre-Emergence Test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, thestated amount of emulsifier is added and the concentrate is diluted withwater to the desired concentration.

Seeds of the test plants are sewn in normal soil. After about 24 hours,the soil is sparyed with the preparation of active compound such thatthe particular amounts of active compound desired are applied per unitarea. The concentration of the spray liquor is chosen such that theparticular amounts of active compound desired are applied in 1000 l ofwater/ha.

After three weeks, the degree of damage to the plants is rated in %damage in comparison to the development of the untreated control.

The figures denote:

-   -   0%=no effect (like untreated control)    -   100%=total destruction

pre-emergence greenhouse g ai/ha Alopecurus Avena fatua EchinochloaSetaria Amaranthus Ex. I-1-4 250 95 90 100 100 90 post-emergencegreenhouse g ai/ha Sugar beet Alopecurus Avena fatua Echinochloa SetariaEx. I-1-14 250 0 80 100 100 100 Ex. I-1-11 250 0 95 90 100 100post-emergence greenhouse g ai/ha Alopecurus Avena fatua EchinochloaSetaria Ex. I-1-7 250 90 95 100 100 Ex. I-1-9 250 95 100 100 100 Ex.I-1-13 250 95 90 100 90 post-emergence greenhouse g ai/ha Sugar beetAlopecurus Avena fatua Digitaria Echinochloa Setaria Ex. I-1-2 125 0 9095 100 100 90 Ex. I-1-1 125 0 95 100 90 100 100 post-emergencegreenhouse g ai/ha Alopecurus Avena fatua Echinochloa Setaria AmaranthusSinapis Ex. I-1-6 250 70 100 100 95 70 — Ex. I-1-8 250 95 95 100 100 7080 Ex. I-1-10 250 100 100 100 100 80 80 Ex. I-1-4 250 100 100 100 100 —70

Example J Plasmopara Test (Grapevine)/Protective

Solvents: 24.5 parts by weight of acetone

-   -   24.5 parts by weight of dimethylacetamide

Emulsifier: 1.0 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate. After thespray coating has dried on, the plants are inoculated with an aqueousspore suspension of Plasmopara viticola and then remain in an incubationcabin at 20° C. and 100% relative atmospheric humidity for 1 day. Theplants are then placed in a greenhouse at about 21° C. and about 90%atmospheric humidity for 4 days. The plants are then moistened andplaced in an incubation cabin for 1 day.

Evaluation is carried out 6 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

TABLE J Plasmopara test (grapevine)/protective Application rate ofactive Active compound compound in g/ha % efficacy Ex. I-1-2 100 100 Ex.I-1-1 100 100 Ex. I-1-14 100 100 Ex. I-1-6 100 94 Ex. I-1-11 100 100 Ex.I-1-12 100 94 Ex. I-1-13 100 94

Example K Venturia Test (Apple)/Protective

Solvents: 24.5 parts by weight of acetone

-   -   24.5 parts by weight of dimethylacetamide

Emulsifier: 1.0 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate. After thespray coating has dried on, the plants are inoculated with an aqueousconidia suspension of the apple scab pathogen Venturia inaequalis andthen remain in an incubation cabin at about 20° C. and 100% relativeatmospheric humidity for 1 day.

The plants are then placed in a greenhouse at about 21° C. and arelative atmospheric humidity of about 90%.

Evaluation is carried out 10 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

TABLE K Venturia test (apple)/protective Application rate of activeActive compound compound in g/ha % efficacy Ex. I-1-2 100 96 Ex. I-1-1100 97 Ex. I-1-6 100 99 Ex. I-1-11 100 100

Example L Critical Concentration Test/Soil Insects Treatment ofTransgenic Plants

Test insect; Diabrotica balteata—larvae in soil

Solvent: 7 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, thestated amount of emulsifier is added and the concentrate is diluted withwater to the desired concentration.

The preparation of active compound is poured onto the soil. Here, theconcentration of the active compound in the preparation is virtuallyimmaterial, only the amount by weight of active compound per volume unitof soil, which is stated in ppm (mg/l), matters. The soil is filled into0.25 l pots, and these are allowed to stand at 20° C.

Immediately after the preparation, 5 pregerminated maize corns of thecultiva YIELD GUARD (trademark of Monsanto Comp., USA) are placed intoeach pot. After 2 days, the appropriate test insects are placed into thetreated soil. After a further 7 days, the efficacy of the activecompound is determined by counting the maize plants that have emerged (1plant=20% activity).

Example M Heliothis virescens Test—Treatment of Transgenic Plants

Solvent: 7 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentration.

Soyabean shoots (Glycine max) of the cultiva Roundup Ready (trademark ofMonsanto Comp. USA) are treated by being dipped into the preparation ofactive compound of the desired concentration and are populated with thetobacco budworm Heliothis virescens while the leaves are still moist.

After the desired period of time, the kill of the insects is determined.

1. A compound of formula (I)

in which Q represents the group N-D, X represents halogen, alkyl,alkoxy, alkenyloxy, alkylthio, alkylsulphinyl, alkylsulphonyl,haloalkyl, haloalkoxy, haloalkenyloxy, nitro, cyano, or optionallysubstituted phenyl, Y represents optionally substituted aryl or hetaryl,W and Z independently of one another represent hydrogen, halogen, alkyl,alkoxy, haloalkyl, haloalkoxy, nitro, or cyano, A represents hydrogen;represents optionally substituted alkyl, alkenyl, alkoxyalkyl,polyalkoxyalkyl, or alkylthioalkyl; represents saturated or unsaturated,optionally substituted cycloalkyl in which one or more ring atoms isoptionally replaced by a heteroatom; or represents optionally halogen-,alkyl-, haloalkyl-, alkoxy-, haloalkoxy-, cyano-, or nitro-substitutedaryl, arylalkyl, or hetaryl, B represents hydrogen, alkyl, oralkoxyalkyl, D represents hydrogen or an optionally substituted radicalselected from the group consisting of alkyl, alkenyl, alkynyl,alkoxyalkyl, polyalkoxyalkyl, alkylthioalkyl, saturated or unsaturatedcycloalkyl in which one or more ring members are optionally replaced byheteroatoms, arylalkyl, aryl, hetarylalkyl, and hetaryl, and Grepresents halogen or nitro.
 2. A compound of formula (I) according toclaim 1, in which Q represents the group N-D, W represents hydrogen,halogen, C₁-C₆-alkyl, or C₁-C₆-alkoxy, X represents halogen,C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, cyano, oroptionally halogen-, C₁-C₆-alkyl-, C₁-C₆-alkoxy-, C₁-C₄-haloalkyl-,C₁-C₄-haloalkoxy-, nitro-, or cyano-substituted phenyl, Y represents oneof the radicals

in which V¹ represents hydrogen, halogen, C₁-C₁₂-alkyl, C₁-C₆-alkoxy,C₁-C₆-alkylthio, C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl,C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy, nitro, cyano, or phenyl that isoptionally mono- or disubstituted by halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy,C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy, nitro, or cyano, V² and V³independently of one another represent hydrogen, halogen, C₁-C₆-alkyl,C₁-C₆-alkoxy, C₁-C₄-haloalkyl, or C₁-C₄-haloalkoxy, Z representshydrogen, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,C₁-C₆-haloalkoxy, nitro, or cyano, A represents optionallyhalogen-substituted C₁-C₁₂-alkyl, C₃-C₈-alkenyl,C₁-C₁₀-alkoxy-C₁-C₈-alkyl, poly-C₁-C₈-alkoxy-C₁-C₈-alkyl, orC₁-C₁₀-alkylthio-C₁-C₆-alkyl; represents optionally halogen-,C₁-C₆-alkyl-, or C₁-C₆-alkoxy-substituted C₃-C₈-cycloalkyl in which oneor two ring members that are not directly adjacent are optionallyreplaced by oxygen and/or sulphur; or represents optionally halogen-,C₁-C₆-alkyl-, C₁-C₆-haloalkyl-, C₁-C₆-alkoxy-, C₁-C₆-haloalkoxy-,cyano-, or nitro-substituted phenyl, phenyl-C₁-C₆-alkyl; or representshydrogen if D is not hydrogen, B represents hydrogen, C₁-C₁₂-alkyl, orC₁-C₈-alkoxy-C₁-C₆-alkyl, D represents hydrogen; represents optionallyhalogen-substituted C₁-C₁₂-alkyl, C₃-C₈-alkenyl, C₃-C₈-alkynyl,C₁-C₁₀-alkoxy-C₂-C₈-alkyl, poly-C₁-C₈-alkoxy-C₂-C₈-alkyl, orC₁-C₁₀-alkylthio-C₂-C₈-alkyl; represents optionally halogen-,C₁-C₄-alkyl-, C₁-C₄-alkoxy-, or C₁-C₄-haloalkyl-substitutedC₃-C₈-cycloalkyl in which one ring member is optionally replaced byoxygen or sulphur; or represents optionally halogen-, C₁-C₆-alkyl-,C₁-C₆-haloalkyl-, C₁-C₆-alkoxy-, C₁-C₆-haloalkoxy-, cyano-, ornitro-substituted phenyl, and G represents chlorine, bromine or nitro.3. A compound of formula (I) according to claim 1, in which Q representsthe group N-D, W represents hydrogen, chlorine, bromine, or C₁-C₄-alkyl,X represents fluorine, chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy,C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy, or cyano, Y represents the radical

in which V¹ represents hydrogen, fluorine, chlorine, bromine,C₁-C₆-alkyl, C₁-C₄-alkoxy, C₁-C₂-haloalkyl, C₁-C₂-haloalkoxy, nitro, orcyano; or represents phenyl that is optionally mono- or disubstituted byfluorine, chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₂-haloalkyl,C₁-C₂-haloalkoxy, nitro, or cyano, and V² represents hydrogen, fluorine,chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₂-haloalkyl, orC₁-C₂-haloalkoxy, Z represents hydrogen, fluorine, chlorine, bromine,C₁-C₄-alkyl, C₁-C₂-haloalkyl, C₁-C₄-alkoxy, or C₁-C₂-haloalkoxy, Arepresents C₁-C₁₀-alkyl or C₁-C₈-alkoxy-C₁-C₆-alkyl, each of which isoptionally mono- to pentasubstituted by fluorine or chlorine; representsC₃-C₇-cycloalkyl that is optionally mono- or disubstituted by fluorine,chlorine, C₁-C₄-alkyl, or C₁-C₄-alkoxy and in which one ring member isoptionally replaced by oxygen or sulphur; or represents phenyl orphenyl-C₁-C₄-alkyl, each of which is optionally mono- or disubstitutedby fluorine, chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₁-C₄-alkoxy, or C₁-C₄-haloalkoxy; or represents hydrogen if D is nothydrogen, B represents hydrogen or C₁-C₆-alkyl, D represents hydrogen;represents C₁-C₁₀-alkyl, C₃-C₆-alkenyl, C₁-C₄-alkoxy-C₂-C₄-alkyl, orC₁-C₄-alkylthio-C₂-C₄-alkyl, each of which is optionally mono- topentasubstituted by fluorine or chlorine; represents C₃-C₇-cycloalkylthat is optionally mono- or disubstituted by fluorine, chlorine,C₁-C₄-alkyl, C₁-C₄-alkoxy, or C₁-C₂-haloalkyl and in which one methylenegroup is optionally replaced by oxygen or sulphur; or represents phenylthat is optionally mono- or disubstituted by fluorine, chlorine,bromine, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, orC₁-C₄-haloalkoxy, and G represents chlorine, bromine, or nitro.
 4. Acompound of formula (I) according to claim 1, in which Q represents thegroup N-D, W represents hydrogen, chlorine, methyl, or ethyl, Xrepresents chlorine, methyl, ethyl, n-propyl, isopropyl, methoxy,ethoxy, n-propoxy, isopropoxy, trifluoromethyl, difluoromethoxy,trifluoromethoxy, or cyano, Y represents the radical

in which V¹ represents hydrogen, fluorine, chlorine, bromine, methyl,ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, methoxy,ethoxy, n-propoxy, isopropoxy, trifluoromethyl, trifluoromethoxy, nitro,or cyano, and V² represents hydrogen, fluorine, chlorine, methyl, ethyl,n-propyl, isopropyl, methoxy, ethoxy, trifluoromethyl, ortrifluoromethoxy, Z represents hydrogen, fluorine, chlorine, methyl,ethyl, n-propyl, or methoxy, A represents C₁-C₆-alkyl orC₁-C₂-alkoxy-C₁-C₂-alkyl; represents C₃-C₆-cyclo-alkyl in which one ringmember is optionally replaced by oxygen or sulphur; or representshydrogen if D is not hydrogen, B represents hydrogen, methyl, or ethyl,D represents hydrogen, methyl, ethyl, n-propyl, isopropyl, cyclopropyl,cyclopentyl, or cyclohexyl, and G represents chlorine or nitro.
 5. Acompound of formula (I) according to claim 1, in which Q represents thegroup N-D, W represents hydrogen, chlorine, or methyl, X representschlorine, methyl, or ethyl, Y represents the radical

in which V² represents chlorine or methyl, and V² represents hydrogen orchlorine, Z represents hydrogen or methyl, A represents methyl, ethyl,propyl, isopropyl, n-butyl, isobutyl, s-butyl, tert-butyl, cyclopropyl,cyclopentyl, or cyclohexyl, B represents methyl, D represents hydrogen,and G represents chlorine or nitro.
 6. A pesticide comprising one ormore compounds of formula (I) according to claim 1 and one or moreextenders and/or surfactants.
 7. A herbicide comprising one or morecompounds of formula (I) according to claim 1 and one or more extendersand/or surfactants.
 8. A fungicide comprising one or more compounds offormula (I) according to claim 1 and one or more extenders and/orsurfactants.
 9. A method for controlling animal pests comprisingallowing an effective amount of a compound of formula (I) according toclaim 1 to act on animal pests and/or their habitat.
 10. A method forcontrolling unwanted vegetation comprising allowing an effective amountof a compound of formula (I) according to claim 1 to act on unwantedvegetation and/or its habitat.
 11. A method for controlling fungicomprising allowing an effective amount of a compound of formula (I)according to claim 1 to act on fungi and/or their habitat.